Day: August 24, 2021

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 70298-88-3, name is 2,2-Dimehtyl-N-pyridin-3-yl-propionamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

In the three bottle,3-Pivalamidopyridine (20.0 g, 112.2 mmol) was dissolved in anhydrous tetrahydrofuran (200 mL).In nitrogen protection, the temperature drops to -78 C,N-butyllithium (17.8 g, 280.5 mmol) was added dropwise and the solution was dropped.Slowly warming to 0C for 3 hours,Then cool down to -78 C,N-methyl-N-methoxyacetamide (17.4 g, 168.3 mmol) was added dropwise.After completion of the dropwise addition, the reaction was slowly warmed to room temperature for 10 h.After the reaction was completed, the reaction was quenched with 1N hydrochloric acid, extracted with ethyl acetate (100 mL×3), and the organic phase was collected and washed with saturated brine (100 mL×1).The solvent was evaporated under reduced pressure to give crude N-(4-ethanhydrin-3-yl)trimethylacetamide.The crude product was applied on a silica gel column (mobile phase: PE_EA=5:1) to obtain 11.2 g of a pure product with a yield of 45.4%.

With the rapid development of chemical substances, we look forward to future research findings about 70298-88-3.

Reference:
Patent; Guizhou University; Liu Li; Huang Zhuyan; Yue Yi; (8 pag.)CN107382839; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31181-79-0, (3-Fluoropyrid-2-yl)methanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 31181-79-0, blongs to pyridine-derivatives compound. Product Details of 31181-79-0

Preparation 60; 2-Chloromethyl-3-fluoro-pyridine EPO Dissolve (3-fluoro-pyridin-2-yl)-methanol (215 mg, 1.69 mmol) in dichloromethane (10 mL) and cool to 0 0C. Add thionyl chloride (160 muL, 2.20 mmol) and stir the reaction for one hour. Add dichloromethane (50 mL) and stir the reaction with saturated aqueous sodium bicarbonate (2 x 40 mL) and brine (2 x 40 mL). Separate and dry the organic portion over magnesium sulfate, filter, and concentrate under reduced pressure to provide 198 mg (80%) of product, which is used without further purification. MS: m/z 146, 148 [C6H5ClFN + I]+; 1H NMR (300 MHz, CDCl3): delta 8.41-8.44 (m, IH), 7.41-7.47 (m, IH), 7.28-7.34 (m, IH), 4.75 (d, J = 2.0 Hz, 2H); 19F NMR (282 MHz, CDCl3): delta -123.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31181-79-0, (3-Fluoropyrid-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1207557-36-5, 6-Bromo-4-methoxypyrazolo[1,5-a]pyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 1207557-36-5, blongs to pyridine-derivatives compound. Recommanded Product: 1207557-36-5

To a solution of 6-bromo-4-methoxypyrazolo[i,5-a]pyridine (Intermediate P1; 2.00g, 227.1 mmol) and 1 -methyl-4- (4,4, 5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (2.02 g, 208.1 mmol) in dioxane (10 mL) was added 2 M Na2CO3(aq) (8.1 mL, 17.6 mmol) and Pd(PPh3)4 (4.584 g, 3.967 mmol). The reaction mixture was purged with nitrogen for 2 mm, sealed and heated at 90 C for 4 h. After cooling to ambient temperature, the reaction mixture was diluted with water (50 mL) and stirred for 30 mm. The resulting suspension was vacuum filtered, rinsed sequentially with water (2 x 20 mL) and Et20 (2 x 10 mL) to yield the crude title compound, which was used in the next step without further purification. MS (apci), m/z = 229.1 (M+H).

The synthetic route of 1207557-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 88511-27-7, Adding some certain compound to certain chemical reactions, such as: 88511-27-7, name is 4-Amino-3-iodopyridine,molecular formula is C5H5IN2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 88511-27-7.

To a solution of 4-aminopyridine (1a, 37.65 g, 0.4 mole) in HOAc (200 mL) was added iodine monchloride (130 g, 0.8 mole) portionwise. The reaction mixture was stirred at 45 C. for 20 h, then diluted with water (500 mL). The mixture was cooled to 0 C., and basified 30% NaOH to pH=9-10. The solution was extracted with EtOAc (1 L×2) and the combined extracts were washed with 15% Na2S2O3 (400 mL×2), water, brine, dried over Na2SO4, and evaporated in vacuo to give 1b (62 g) as a light yellow solid. ES-MS m/z 221 (MH+). [0185] Into a pressure flask was added 1b (4.4 g, 20 mmol), cupric iodide (228 mg, 1.2 mmol), (trimethylsilyl)acetylene (7.08 g, 72 mmol), triethylamine (200 mL) and DMF (80 mL). The mixture was stirred under nitrogen for 10 min, followed by addition of Pd(PPh3)2Cl2 (0.84 g, 1.2 mmol). The mixture was then stirred to 70 C. for 5 h, and then diluted with ethyl acetate (600 mL). The solution was washed with H2O (250 mL×2), brine (250 mL), dried over Na2SO4, and evaporated in vacuo to give crude product which was purified by flash chromatography (100% CH2Cl2 to 2% MeOH in CH2Cl2) to afford Compound 1c (2. 97 g, 78%) as a light brown solid. 1H NMR (CDCl3) delta 8.37 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 6.53 (d, J=5.6 Hz, 1H), 4.67 (bs, 2H), 0.27 (s, 9H). ES-MS m/z 191 (MH+). [0186] Into an ice-cold solution of 1c (1.35 g, 7.1 mmol) in THF (50 mL) was added 95% NaH (1.86 g, 8.5 mmol). The mixture was stirred at 0 C. for 10 min, rt for 10 min, then cooled back to 0 C. (Boc)2O (1.86 g, 8.5 mmol) was added and the mixture was stirred at 0 C. for 30 min and then rt for 2 h. Additional 95% NaH (0.08 g, 3.5 mmol) and (Boc)2O (0.2 g, 0.92 mmol) were added and the mixture was stirred at rt for another 2 h. The reaction was then quenched slowly with saturated NaHCO3 (10 mL), extracted with ethyl acetate (200 mL×2). The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (EtOAc/hexane; 1:3) to give 1d (0.67 g). ES-MS m/z 219 (MH+). [0187] To a solution of 1d (1.3 g, 4.5 mmol) in DMF (20 mL) was added cupric iodide (0.85 g, 4.5 mmol). The mixture was stirred at 80 C. for 6 h and then filtered. The filtrate was extracted with ethyl acetate (100 mL×3), and the organic layer was washed with H2O, brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (Ethyl acetate/hexane; 1:3) to give Compound 1e (0.25 g, 26%). 1H NMR (CDCl3) delta 8.89 (s, 1H), 8.47 (d, J=5.8 Hz, 1H), 7.98 (d, J=5.7 Hz, 1H), 7.62 (d, J=3.7 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 1.69 (s, 9H). ES-MS m/z 219 (MH+). [0188] To a solution of 1e (0.178 g, 0.82 mmol) in methylene chloride (5 mL) was added TFA (1.0 mL) slowly. The mixture was stirred at rt for 1.5 h, and The solvent was evaporated to obtain 5-azaindole 1f as a white solid (0.18 g, 95%). 1H NMR (CDCl3) delta 8.97 (s, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.35 (d, J=5.7 Hz, 1H), 7.29 (m, 1H), 6.68 (d, J=3.3 Hz, 1H). ES-MS m/z 119 (MH+). [0189] A mixture of Compound 1f (0.26 g, 2.2 mmol) and cesium carbonate (1.43 g, 4.4 mmol) in DMF (10 mL) was stirred at rt for 10 min, and then 3-methoxypropylbromide (0.40 g, 2.64 mmol) was added. The reaction mixture was stirred at 60 C. for 3 h. The solvent was evaporated and the residue was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with water (3×50 mL), brine (2×50 mL), then dried (Na2SO4) and evaporated in vacuo to give a brown oil. The crude product was purified by flash column chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1g (0.26 g, 62%) as light brown oil. 1H NMR (CDCl3) delta 8.91 (s, 1H), 8.31 (d, J=5.8 Hz, 1H), 7.27 (s, 1H), 7.11 (d, J=3.2 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 4.25 (t, J=6.7 Hz, 2H), 3.32 (s, 3H), 3.25 (t, J=5.7 Hz, 2H), 2.05 (m, 2H). ES-MS m/z 191(MH+). [0190] Oxalyl chloride (3 mL) was added slowly to a solution of compound 1g (0.22 g, 1.14 mmol) in ether (5 mL). The mixture was heated to 48 C. in a pressure tube overnight. TLC shown that some starting materials were still present. Additional 0.5 mL of oxalyl chloride was added and stirring was continuted at 48 C. for another night. The mixture was then cooled down to rt, to which methanol (3 mL) was added. The mixture was heated to 48 C. and stirred for 2 h. The volatiles removed under vacuo and the residue was purified by flash chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1h (0.15 g, 48%) as a white solid. 1H NMR (CDCl3) delta 8.51 (d, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.37 (m, 1H), 4.34 (t, J=6.8 Hz, 2H), 3.97 (s, 3H), 3.35 (s, 3H), 3.30 (t, J=5.7 Hz, 2H), 2.12 (m, 2H). ES-MS m/z 277 (MH+). [0191] The alpha-ketoester Compound 1h (53.8 mg, 0.20 mmol) and amide Compound 1i (23 mg, 0.14 mmol) were combined in dry THF (3 mL) under argon and cooled with an ice bath as a solution of 1.0 M potassium t-butoxide in THF (1 mL, 1 mmol) was added dropwise. The mixture was stirred at 0 C. for 30 …

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 88511-27-7, 4-Amino-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Han-Cheng; Maryanoff, Bruce E.; Ye, Hong; US2004/192718; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 609-71-2, Adding some certain compound to certain chemical reactions, such as: 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid,molecular formula is C6H5NO3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 609-71-2.

A stirred suspension of NaH 60% dispersion in mineral oil (206 mg, 5.14 mmol), washed twice with distilled n-hexane and once with Et20 in 2 mL of anhydrous DMF under N2 atmosphere was treated dropwise with a solution containing the 2-hydroxynicotinic acid (600 mg, 4.31 mmol) in 5 mL of anhydrous DMF. The mixture was left under stirring at room temperature for 2h and then 3,4-difluoro-benzylbromide (1.06 g, 5.14 mmol) was added and the mixture stirred and heated at 50C for 1 6h. After the mixture was concentrated under reduced pressure and the residue was treated with water to give a solid, which was collected by vacuum filtration. Next the solid was refluxed for 4h in aq. 10% NaOH (10 mL) and the resulting mixture was cooled and made acid with 1 N aq.HCI. The white solid formed was collected by filtration and washed with nhexane and Et20, giving the derivative 3.9 as white solid (857 mg, 3.23 mmol, 75% yield).1HNMR (400 MHz, DMSO-d6): 65.30 (5, 2H, CH2); 6.78 (t, 1H, J = 6.9 Hz, Ar);7.22-7.24 (m, 1H, Ar); 7.41 -7.53 (m, 2H, Ar); 8.41 (d, 2H, J = 6.9 Hz, Ar) ppm.Anal. Calcd for C13H9NO3F2: C, 58,87%; H, 3.42%; N, 5.28%; Found: C, 58,99%; H, 3.47%; N, 5.43%

According to the analysis of related databases, 609-71-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (63 pag.)WO2016/198597; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59576-26-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 59576-26-0, name is 1-(4-Methylpyridin-2-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: In a high pressure vial charged with a solution of 1-(4-methylpyridin-2-yl)ethanone (1.0 equiv.) and EtOH (0.1 equiv) in DCM (2.0M) was added DAST (2.5 equiv.). The reaction was heated to 30 oC and heated for 48 hrs. LCMS analysis indicated the formation of the desired product (MH+?157.9, Rt?0.54 min). The reaction was diluted with DCM and quenched with NaHCO3, slowly at 0oC. The phases were separated and the aqueous layer was washed with DCM (2×). The combined organics were dried over MgSO4, filtered, and concentrated. The crude material was purified via flash chromatography over silica gel eluting with heptanes and 0-100percent ethyl acetate gradient. Isolated 2-(1,1-difluoroethyl)-4-methylpyridine in 27percent yield. LCMS (m/z) (M+H)=157.9, Rt=0.54.

According to the analysis of related databases, 59576-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1082040-63-8, Adding some certain compound to certain chemical reactions, such as: 1082040-63-8, name is 3-Iodo-1H-pyrazolo[3,4-c]pyridine,molecular formula is C6H4IN3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1082040-63-8.

B. Tert-butyl 2-(3-iodo-I H-pyrazolo[3,4-c]pyridi n-I -yI)acetateTo a suspension of 3-iodo-IH-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added dropwise at RT tert-butyl 2- bromoacetate (4.06 mL, 27.5 mmol). The resulting mixture was refluxed for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated and purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1, then 2:1, then 1:1) to afford the title compound. MS (LC/MS): 360.0 [M+H]+; tR (HPLC conditions d): 2.93 mm.

According to the analysis of related databases, 1082040-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; VULPETTI, Anna; WO2014/2051; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15854-87-2, name is 4-Iodopyridine, molecular formula is C5H4IN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. name: 4-Iodopyridine

General procedure: A mixture of aryl halide (1.0 mmol), K4[Fe(CN)6](0.22 mmol), 0.05 g [PS-ttet-Pd(II)], and sodium carbonate(1.0 mmol) was stirred in 5 cm3 DMF at 120 C for 1 h under an argon atmosphere. To the aryl nitrile compound generated in situ was added sodium azide (1.5 mmol) and the mixture was stirred at 120 C for appropriate time. After completion of the reaction (as indicated by TLC), the catalyst was centrifuged, washed with EtOH and the residue was diluted with 35 cm3 ethyl acetate and 20 cm3 HCl(4 N) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with 25 cm3 ethyl acetate. The combined organic layer was washed with 8 cm3 water and concentrated to give a crude product. Column chromatography using silica gel gave thepure product. All products were characterized by 1H NMR and melting point which were in agreement with literature

With the rapid development of chemical substances, we look forward to future research findings about 15854-87-2.

Reference:
Article; Tajbakhsh, Mahmood; Alinezhad, Heshmatollah; Nasrollahzadeh, Mahmoud; Kamali, Taghi A.; Monatshefte fur Chemie; vol. 147; 12; (2016); p. 2135 – 2142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 155790-01-5, name is 5-Bromo-N,4-dimethyl-3-nitropyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-N,4-dimethyl-3-nitropyridin-2-amine

5-Bromo-N2,4-dimethylpyridine-2,3-diamineTo a solution of 5-bromo-N,4-dimethyl-3-nitropyridin-2-amine (1000 mg, 4.06 mmol) in EtOH (20 mL) at RT, SnCI2-2 H20 (3668 mg, 16.26 mmol) was added. The reaction mixture was stirred for 1 h. The solvent was evaporated under reduce pressure and saturated NaHC03solution was added to pH=7 then it was extracted with EtOAc (3×40 mL), and the combined organic layers were washed once with brine. The organic layer was concentrated to give 720 mg (82%) of the title compound. LC-MS m/z 216.0, 218.0 (M+H)+, 0.54 (ret. time).

The synthetic route of 155790-01-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1101120-37-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1101120-37-9, name is Pyrazolo[1,5-a]pyridin-5-amine, molecular formula is C7H7N3, molecular weight is 133.15, as common compound, the synthetic route is as follows.

Decarboxylation of ester 3l (1.29 g, 2.98 mmol), except with carrying out the aqueous extraction from pH 12, gave pyrazolo[1,5-a]pyridin-5-amine (7l) as a pale brown solid (310 mg, 78%). 1H NMR delta (400 MHz, CDCl3) 8.23 (d, J = 7.4 Hz, 1H), 7.79 (d, J = 2.0 Hz, 1H), 6.58 (d, J = 2.4 Hz, 1H), 6.22 (dd, J = 7.4, 2.4 Hz, 1H), 6.13 (d, J = 2.0 Hz, 1H), 3.81 (s, 2H). LC-MS (APCI+) 134 (MH+, 100%). A solution of NaNO2 (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of 7l (40 mg, 0.30 mmol) and CuCl (74 mg, 0.75 mmol) in concentrated HCl (1 mL) at 0 C over 2 min. After 30 min, the reaction mixture was heated to 80 C for 15 min, and then cooled to room temperature, basified to pH 10 with 1 M NaOH, filtered through a plug of celite and washed with CH2Cl2. The layers of the filtrate were separated and the aqueous layer extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1,5-a]pyridine (7o) as a white solid (6 mg, 13%). 1H NMR delta (400 MHz, CDCl3) 8.38 (d, J = 7.4 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.71 (dd, J = 7.4, 2.2 Hz, 1H), 6.47 (d, J = 1.8 Hz, 1H). LC-MS (APCI+) 153 (MH+ with 35Cl, 100%), 155 (MH+ with 37Cl, 30%). Vilsmeier reaction of 7o (6 mg, 0.039 mmol) gave 4o as a white solid (7 mg, 100%).

Statistics shows that 1101120-37-9 is playing an increasingly important role. we look forward to future research findings about Pyrazolo[1,5-a]pyridin-5-amine.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem