Day: February 18, 2021

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. 504-24-5, name is 4-Aminopyridine, molecular formula is C5H6N2, 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. Quality Control of 4-Aminopyridine

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¡Á2) and the combined extracts were washed with 15% Na2S2O3 (400 mL¡Á2), 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¡Á2), 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¡Á2). 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¡Á3), 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¡Á50 mL), brine (2¡Á50 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 …

With the rapid development of chemical substances, we look forward to future research findings about 504-24-5.

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

Electric Literature of 54221-96-4, 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. 54221-96-4, name is 6-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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.

General procedure: General procedure: 8-Hydrazinocaffeine (3) (112 mg;0.5 mmol) and carbonyl compound (1 mmol; 2 eq.) were mixedin ethanol (20 mL, containing 0.2 mL of acetic acid) and heated at 75 omicronC for 3 days. After cooling down, reaction mixture was evaporatedto dryness and solid residue was suspended in diethyl ether(50 mL), filtered off, washed with additional portion of diethylether (3 25 mL) and dried in vacuo at 50 C to obtain the hydrazone.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 54221-96-4, 6-Methoxypicolinaldehyde.

Reference:
Article; Kaplanek, Robert; Jakubek, Milan; Rak, Jakub; Kejik, Zden?k; Havlik, Martin; Dolensky, Bohumil; Frydrych, Ivo; Hajduch, Marian; Kola?, Milan; Bogdanova, Kate?ina; Kralova, Jarmila; D?ubak, Petr; Kral, Vladimir; Bioorganic Chemistry; vol. 60; (2015); p. 19 – 29;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65719-09-7, Methyl 2-methylnicotinate, 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, Computed Properties of C8H9NO2, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO2

a) 2-methylnicotinic Acid Following the procedure of Example 1(g), except substituting methyl-2-methylnicotinate for N-(4-pyridinylmethoxycarbonyl)-L-leucine methyl ester, the title compound was prepared as a white solid (1.6 g, 100percent). MS (ESI): 138.2 (M+H)+.

The synthetic route of 65719-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Halbert, Stacie Marie; Michaud, Evelyne; Thompson, Scott Kevin; Veber, Daniel Frank; US2002/49316; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1196157-51-3, Adding some certain compound to certain chemical reactions, such as: 1196157-51-3, name is 2-Amino-6-bromonicotinic acid,molecular formula is C6H5BrN2O2, 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 1196157-51-3.

Step 1: 2-Amino-6-bromo-5-chloronicotinic acid N-Chlorosuccinimide (2.78 g, 20.8 mmol) was added to a solution of 2-amino-6-bromonicotinic acid (4.51 g, 20.8 mmol, Ark Pharm Inc. Arlington Heights, Ill., USA) in DMF (75 mL), and the resulting mixture was heated at 70 C. for 2.5 h. Heating was then stopped, and stirring was continued for 16 h. The reaction mixture was subsequently poured into ice water. After the ice had melted, the resulting slurry was filtered through a fritted glass funnel. The collected solids were air-dried, providing 2-amino-6-bromo-5-chloronicotinic acid: 1H NMR (400 MHz, DMSO-d6) delta 8.05 (s, 1H), 7.64 (br. s, 2H). m/z (ESI, +ve) 250.9 (M+H)+.

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. 1196157-51-3, 2-Amino-6-bromonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56026-36-9, Methyl 6-(hydroxymethyl)nicotinate, 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, 56026-36-9, blongs to pyridine-derivatives compound. Product Details of 56026-36-9

6-hydroxymethyl nicotinic acid methyl ester (11 ) (10.0 g, 59.8 mmol) was azeotroped with acetonitrile ( 2 x 100 mL) then dissolved in (0261) dichloromethane (alcohol free, 150 mL) and treated with (0262) diisopropylethylamine (12.5 mL, 71 .8 mmol) followed by 2-cyanoethyl-N,N- diisopropylchlorophosphoramidite (13.4g, 56.8 mmol). The reaction mixture was stirred at RT, under argon for 1 .5 hours. TLC (1 : 1 hexane: EtOAc, visualised by PMA/heat) showed reaction completion (SM Rf ~ 0.3, prod Rf ~ 0.5). (0263) The mixture was washed with sat. NaHC03(aq) (100 mL) and the layers were separated. The organic phase was washed with 100 mL sat. then dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to give a brown oil. This was triturated with pentane (2 x 150 mL). (0264) The crude material was purified by flash column chromatography on pre- equilibrated silica gel (1 : 1 EtOAc : pentane + 1 % NEt3) eluting with 1 : 1 EtOAc : pentane, the crude product was loaded in DCM. Product containing fractions were selected by TLC and concentrated in vacuo to give a colourless oil. This was azeotroped with MeCN and dried on the freeze-drier overnight to give 12 (6.55g, 30%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56026-36-9, its application will become more common.

Reference:
Patent; LINK TECHNOLOGIES LIMITED; MCGEOCH, Grant; MCKEEN, Catherine; OSNOWSKI, Andrew; WILSON, Jennifer; WO2015/132577; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, molecular weight is 164.03, as common compound, the synthetic route is as follows.Application In Synthesis of 3-(Chloromethyl)pyridine hydrochloride

A mixture of ethyl 3-[3-ethoxy-1-(4-hydroxy-3-methoxybenzyl)-1H-pyrazol-4-yl]propionate (505 mg), 3-picolyl chloride hydrochloride (476 mg), potassium carbonate (601 mg) and N,N-dimethylformamide (10 ml) was stirred overnight at room temperature. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with saturated brine, dried (MgSO4) and concentrated. The residue was applied to silica gel column chromatography and compound G (531 mg, yield 83%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. NMR(CDCl3)delta:1.21 (3H, t, J=7.0 Hz), 1.37 (3H, t, J=7.0 Hz), 2.47-2.55 (2H, m), 2.61-2.69 (2H, m), 3.84 (3H, s), 4.09 (2H, q, J=7.0 Hz), 4.22 (2H, q, J=7.0 Hz), 4.99 (2H, s), 5.13 (2H, s), 6.68 (1H, dd, J=8.0, 2.2 Hz), 6.77 (1H, d, J=2.2 Hz), 6.84 (1H, d, J=8.0 Hz), 6.95 (1H, s), 7.31 (1H, dd, J=8.0, 4.8 Hz), 7.79 (1H, dt, J=8.0, 1.8 Hz), 8.57 (1H, d, J=4.8 Hz), 8.67 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6959-48-4, 3-(Chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1445254; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1480-64-4, 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.1480-64-4, name is 3-Chloro-2-fluoropyridine, molecular formula is C5H3ClFN, molecular weight is 131.54, as common compound, the synthetic route is as follows.

Example 97 (4S,6S)-4-(5-((3-chloropyridin-2-yl)oxy)-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine The title compound was synthesized using steps and procedures analogous to those described in Method M (Example 92) above, but using 3-chloro-2-fluoropyridine (Matrix) in step 5. MS m/z=422 [M]+. Calculated for C17H13ClF5N3O2: 421.75. 1H NMR (300 MHz, CHLOROFORM-d) ppm 2.19 (t, J=13.15 Hz, 1H) 2.69 (d, J=13.74 Hz, 1H) 4.18 (d, J=8.92 Hz, 3H) 4.34-4.58 (m, 1H) 4.61-4.86 (m, 1H) 6.98 (dd, J=7.38, 4.90 Hz, 1H) 7.12 (d, J=8.62 Hz, 2H) 7.30 (d, J=7.31 Hz, 2H) 7.76 (d, J=7.60 Hz, 1H) 8.00 (d, J=4.82 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 1480-64-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
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. 24100-18-3, name is 2-Bromo-3-methoxypyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 24100-18-3

262 mL of conc. sulfuric acid was cooled down to -2C, and 262 mL of 90 % nitric acid was carefully added thereto. Subsequently, 65.3 g (corresponding to 0.347 mmol) of 2-bromo-3-methoxypyridine was carefully added thereto. After the reaction mixture was stirred in an ice bath for 10 minutes, the mixture was stirred at room temperature for 30 minutes, and then was heated to 55C and further stirred for 1.5 hours. After the reaction solution was cooled to room temperature, the reaction solution was poured little by little into crushed ice to generate precipitates. The precipitates were filtered and washed with water, and then dried over phosphorous pentoxide under reduced pressure, to obtain 55.7 g (corresponding to 0.239 mol) of 2-bromo-3-methoxy-6-nitropyridine (Fig. 3, Step 2).

The synthetic route of 24100-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nihon Medi-Physics Co., Ltd.; EP2213671; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 200064-11-5, 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. 200064-11-5, name is 4-(5-Bromo-2-pyridyl)morpholine, molecular formula is C9H11BrN2O, 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.

General procedure: To a stirred solution of the title compound of Preparative Example 1 (0.150 g, 1 eq) in dry 1 ,4- dioxane (5 mL) was added the commercially available 4-(6-bromobenzo[d]thiazoI-2- yl)morpholine (1 eq), sodium tert-butoxide (3 eq) and the mixture was degassed for 10 minutes under N2 atmosphere. To this reaction mixture was added Pd2(dba)3 (0.05 eq) and Ru-Phos (0.1 eq) and the mixture was heated to 100C until the completion of the reaction. After the completion of the reaction, the reaction mixture was filtered through a celite bed, and washed with EtOAc. The filtrate was concentrated and the crude product was purified by column chromatography or preparative HPLC to afford title compound 6 as indicated in table 2.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 200064-11-5, 4-(5-Bromo-2-pyridyl)morpholine.

Reference:
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (220 pag.)WO2019/134978; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 791644-48-9, 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. 791644-48-9, name is 2-Chloro-5-fluoronicotinonitrile, molecular formula is C6H2ClFN2, 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.

Step 3. 5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine 2-Chloro-5-fluoro-3-pyridinecarbonitrile (15.3 g, 98 mmol) was dissolved in 1-butanol (300 mL), and then hydrazine monohydrate (16.82 mL, 293 mmol) was added, followed by hydrochloric acid (4N in dioxane) (0.244 mL, 0.977 mmol). The reaction mixture was maintained at 70 C for 4 hours, and the resulting yellow crystalline solid was collected by filtration (12.5 g, 84 % yield). MS (m/z) 153 (M+H+). 1H NMR (400 MHz, DMSO-d6) delta ppm 5.56 (s, 2 H), 7.97 (dd, 1 H), 8.39(m, 1 H), 12.07 (s, 1 H).

According to the analysis of related databases, 791644-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; HAILE, Pamela, A.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SINGHAUS, Robert, R.; WANG, Gren, Z.; (83 pag.)EP2680844; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem