Day: April 19, 2022

Related Products of 76006-11-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine. A new synthetic method of this compound is introduced below.

Trimethylaluminum (23.9 ml_, 47.8 mmol, 2M in toluene) was added to a vigorously stirred solution of 7-chloro-1 H-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1 .38 g, 1.19 mmol) in THF (109 ml.) under argon. The reaction mixture was stirred at 65C for 16 h. The mixture was cooled to RT and poured into sat. aq. NH4CI. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried (Phase separator) and concentrated under reduced pressure to give 7-methyl-1 H-pyrazolo[3,4- c]pyridine as a solid. MS (LC-MS): 134 [M+H]+; tR (HPLC conditions d): 0.25 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76006-11-6, 7-Chloro-1H-pyrazolo[3,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FLOHR, Stefanie; HOMMEL, Ulrich; LORTHIOIS, Edwige, Liliane, Jeanne; MAIBAUM, Juergen, Klaus; OSTERMANN, Nils; RANDL, Stefan, Andreas; VULPETTI, Anna; QUANCARD, Jean; WO2014/2052; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 956010-87-0, Adding some certain compound to certain chemical reactions, such as: 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine,molecular formula is C7H4F3N3, 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 956010-87-0.

Trifluoroacetic anhydride (2.6 mL, 18.7 mmol) was added to a solution of tetrabutylammonium nitrate (5.7 g, 18.7 mmol) in dichloromethane (50 mL) cooled to 0C in an ice bath. After 5 minutes, 3-(trifluoromethyl)-lH-pyrazolo[3,4- b]pyridine (0.5 g, 2.67 mmol) was added portionwise. The resulting solution was stirred at room temperature overnight. The reaction mixture was treated with saturated aqueous sodium bicarbonate, and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to an oil. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (2:1) to give 5-nitro-3-(trifluoromethyl)-lH-pyrazolo[3,4-b]pyridine (0.19 g, 31%) as a solid.

According to the analysis of related databases, 956010-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; AHRENDT, Kateri A.; BUCKMELTER, Alexandre J.; DE MEESE, Jason; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen R.; LUNGHOFER, Paul; MORENO, David; NEWHOUSE, Brad; REN, Li; SEO, Jeongbeob; TIAN, Hongqi; WENGLOWSKY, Steven Mark; FENG, Bainian; GUNZNER, Janet; MALESKY, Kim; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; YOUNG, Wendy B.; WO2009/111279; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 179687-79-7, 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 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 3 Preparation of N-[3-Chloro-4-(2-pyridinylmethoxy)]phenyl-2-cyanoacetamide In a 12-L multi-necked flask, 2-pyridyl carbinol (0.13 kg, 1.19 mole, 1.05 eq) was dissolved in acetonitrile (0.88 L) and to it was added potassium hydroxide flakes (85%) (80 g, 1.25 eq). The resulting suspension was warmed to 35 C. A solution of 3-chloro-4-fluoronitrobenzene (0.20 kg, 1.14 mol) in acetonitrile (1.0 L) was added at 35-40 C. The mixture was held for 18 h until reaction completion. The mixture was then cooled back to 20-25 C., quenched with water (4 L) and the resulting slurry was filtered and washed with water (3×200 mL). The resulting product was isolated as a tan solid (251 g, 84% yield). A mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.149 kg, 0.56 mole) and 2% (w/w) of 5% Pt/C (6.0 g, 50% water wet) in tetrahydrofuran (0.895 L) was hydrogenated in a 2-L stainless steel Parr reactor at 25 psi, 25 C. for a minimum of 8 h. The mixture was filtered through a celite pad (50 g, 15 cm diameter) and washed with tetrahydrofuran (0.45 L). The filtrate was distilled to a volume of 0.30 L and the concentrate was transferred to a 2-L multi-neck flask and used as is in the next step. To the 2-L flask equipped with mechanical stirrer, temperature probe, claisen head and condenser was added ethylcyanoacetate (0.421 kg, 3.72 mole, 6.6 eq.). The reaction mixture was heated to (100-115 C.) while removing tetrahydrofuran and ethanol. The temperature was raised to 125 C. and the mixture was held for a minimum of 24 h until the aniline starting material was consumed and no distillate was collected. The mixture was cooled to room temperature over 1 h. At 50-60 C., solids crystallized out and ethyl acetate (0.15 L) was added. The mixture was further cooled to 0-10 C. and held for 1 h. The mixture was filtered on a 15 cm diameter Buchner funnel and washed with 50 mL of the filtrate followed by pre-cooled (0-10 C.) ethyl acetate (0.15 L). The product was dried at 60 C. for a minimum of 16 h in a vacuum oven to give the titled compound (0.12 kg, 71%) as a brown solid. The product was purified by slurrying in cold ethyl acetate (1-1.3 volumes) for 1 hr. 1H NMR: delta (DMSO-d6) 10.31 (s, 1H, NH), 8.58 (dd, 1H, Ar), 7.86 (dt, 1H, Ar), 7.75 (d, 1H, Ar), 7.55 (d, 1H, Ar), 7.39-7.32 (m, 2H, Ar), 7.21 (d, 1H, Ar), 5.25 (s, 2H, OCH2Pyr), 3.88 (s, 2H, NCCH2CO).

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 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine.

Reference:
Patent; Chew, Warren; Papamichelakis, Maria; US2006/270669; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19346-43-1, 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. 19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, molecular formula is C6H5FN2O2, 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.

18. Preparation of 3-Amino-2-fluoro-4-methylpyridine To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid, melting at 63-64 C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDC13): 1 H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13 C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

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 19346-43-1, 2-Fluoro-3-nitro-4-picoline.

Reference:
Patent; DowElanco; US5602075; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 298709-29-2, name is 3,5-Difluoropicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 298709-29-2

Reference Example 15 Synthesis of intermediate compound (107) [Show Image] [Show Image] First step A solution of a compound (106) (1.0 g) in concentrated sulfuric acid (5.4 ml) and water (600 mul) was stirred at 110C for 22 hours, the mixture was poured into ice water, and the precipitated solid was collected by filtration. The solid was washed with water, and naturally dried to afford the compound (107) (1.02 g). 1H-NMR(DMSO-d6) delta: 8.08 (1H, m), 8.60 (1H, m).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 298709-29-2, 3,5-Difluoropicolinonitrile.

Reference:
Patent; Shionogi & Co., Ltd.; EP2305672; (2011); A1;,
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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine, molecular formula is C5H4ClFN2, 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. Product Details of 89510-90-7

To a solution of 2-chloro-5-fluoropyridin-4-amine (1.0 g, 6.82 mmol) in DCM (50 mL) at 0 C was addded TEA (1.046 mL, 7.51 mmol), DMAP (0.083 g, 0.682 mmol) and Boc2O (1.584 mL, 6.82 mmol). The reaction mixture was stirred at room temperature for18 h. The reaction mixture was evaporated under reduced pressure to afford crude product as a black residue. The crude product was purified by silica gel chromatography (eluted with 10% ethyl acetate in petroleum ether) to yield tert-butyl (2-chloro-5-fluoropyridin-4- yl)carbamate 79A (1.0 g, 59.4%). LCMS m/z 247.0 (M+H); rt 0.95 mm; Conditions H.

With the rapid development of chemical substances, we look forward to future research findings about 89510-90-7.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To each reaction tube in a 24-position Bohdan MiniBlock XT was added the appropriate aldehyde (5.0 equiv, 1.15 mmol), which was dissolved in MeCN (1 mL). A solution of 2-(benzo[d][1,3]dioxol-5- yl)pyrimidin-4-amine (8) in MeCN (0.13 M, 1.8 mL, 0.23 mmol, 1.0 equiv) was then dispensed into each tube. ClTi(Oi-Pr)3 (95%, 0.35 mL, 1.38 mmol, 6.0 equiv) was added to each tube, followed by AcOH (3 drops). The reactions were shaken at 450 rpm for 5 minutes, and then solid NaBH(OAc)3 (95%, 257 mg, 1.15 mmol, 5.0 equiv) was added to each tube. The reactions were shaken at 450 rpm for an additional 1.5 hours, and then a solution of 15% aqueous NH4OH (2 mL) and CH2Cl2 (2 mL) were added to each tube causing white solids to precipitate. Shaking was continued for 30 minutes at 450 rpm. Using stackable 24-position Bohdan MiniBlock XTs, the liquid portions of the crude reaction mixtures were passed into phase separators, to which H2O (2 mL) was added. The biphasic mixtures were mixed by hand using pipettes, and then the heavier organic layers were passed from the phase separators into new reaction tubes. The white solids in the original reaction tubes were washed with CH2Cl2 (2 mL) and the washings were passed into the closed phase separators. The biphasic mixtures were again mixed by hand using pipettes and the heavier organic layers were passed into the reaction tubes containing the organic layers from the first separation. The crude reaction mixtures were then placed on a sample concentrator to remove the solvents. TFA/MeOH (1:19, 3 mL) was added to each crude reaction mixture, and the samples were then shaken at 450 rpm for 1 hour. The solutions were then passed onto columns of Dowex 50WX4-400 ion exchange resin (2.0 g, pre-washed with TFA/MeOH (1:99, 5 mL)). Each reaction tube was washed with MeOH (2 mL) and the washings were allowed to pass onto the Dowex columns. The columns were washed with MeOH (3 mL) and the washings discarded. The products were then eluted into collection tubes using a mixture of Et3N/MeOH (1:9, 10 mL). Solvents were removed using a sample concentrator and the products were subjected to reverse-phase preparative HPLC purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Article; Coombs, Thomas C.; Tanega, Cordelle; Shen, Min; Wang, Jenna L.; Auld, Douglas S.; Gerritz, Samuel W.; Schoenen, Frank J.; Thomas, Craig J.; Aube, Jeffrey; Bioorganic and Medicinal Chemistry Letters; vol. 23; 12; (2013); p. 3654 – 3661;,
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. 1057682-05-9, name is (R)-6-(3-Methylpiperazin-1-yl)nicotinonitrile, molecular formula is C11H14N4, 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. HPLC of Formula: C11H14N4

To a stirred solution of 3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoic acid (5.0 g, 21.19mmol, obtained from Example 29, step 3) in dry DMF (40 mL, -8 vol), 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile ( 4.06 g, 20 mmol), EDClHCl (6.08 g, 31.6 mmol),HOBt (3.43 g, 25.4 mmol) and DIPEA (14.5 mL, 84.5 mol) were added at 10-15C andstirred for 22 h. The reaction mixture was quenched with ice cold water (500 mL) andextracted with EtOAc (3 x 70 mL). The combined organic layers were dried over anhydrousNa2S04 and concentrated under reduced pressure to get crude compound. Crude compoundwas stirred with EtOAc (50 mL) for 1 hour at RT, filtered and suck dried. Solid obtained wasagain made slurry with EtOAc. Filtered the solid and washed with EtOAc (50 mL) to afford(50 mL) 6-[(3R)-4-[3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoyl]-3-methyl-piperazin-1-yl]pyridine-3-carbonitrile in 43% yield (3.8g). Chiral HPLC was used to confirm that thecompound is the enantiomer of compound 29. Column used: Lux,5 micron, Cellulose-4 (250X 4.6 mm , 5 micron , Mobile phase: 50:50 n-hexane:(0.1% HCOOH in 1:1ethanol:methanol), Flow rate: 1.0 mL/min, Temperature: 25C. Retention time for Renantiomer= 12.9 min; Retention time for compound 29 = 13.4 min.

With the rapid development of chemical substances, we look forward to future research findings about 1057682-05-9.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17322-91-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 17322-91-7, name is 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one. A new synthetic method of this compound is introduced below.

Dissolve 5-hydroxy-1H-pyrrole[3,2]pyridine (10 mmol) in 40 ml of dichloromethane and add 10 ml to it.Triethylamine, controlled temperature below 10 C, adding 2-chloroacetyl chloride (12 mmol) in dichloromethane to the system, adding dropwiseAfter completion, return to room temperature, stir at room temperature for 10 hours, then wash the reaction system with 50 ml of 5% aqueous sodium carbonate solution, organic phase.After drying with anhydrous Na 2 SO 4 and evaporating the solvent, the obtained solid was separated by flash column chromatography.1.9 g pale yellow 2-chloro-1-(5-Hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-ethanone solid, yield 90%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17322-91-7, its application will become more common.

Reference:
Patent; Sang Qi; (10 pag.)CN108383838; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-61-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1122-61-8 as follows.

Example 15 4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25 C. After completion of the addition, the resulting mixture was at 25 C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-61-8, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5648496; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem