Day: March 22, 2022

Electric Literature of 1221171-96-5, 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 1221171-96-5 as follows.

4-Amino-2-chloro-6-trifluoromethoxypyridine (45); At -78 0C, butyllithium (1.56 M in hexane, 2.2 mL, 3.4 mmol, 1.1 eq) was added dropwise to a solution of 2-chloro-4-iodo-6-trifluoromethoxypyridine (42, 1.0 g, 3.1 mmol) in THF (8 mL) followed after 10 min by benzenesulfonyl azide (0.6 g, 3.4 mmol, 1.1 eq). The reaction mixture was was allowed to reach 25 0C before being treated with a saturated aqueous solution of ammonium chloride (10 mL) and extracted with diethylehter (3 x 8 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford a crude red oil of 4-azido-2-chloro-6- trifluoromethoxypyridine. It was then dissolved in anhydrous diethylether (25 mL) and added dropwise to a suspension of lithium aluminium hydride (130 mg, 3.4 mmol, 1.1 eq) in diehtylether (25 mL). The reaction mixture was heated under reflux for 5 h before being treated with water (10 mL) and extracted with diethylether (3 x 10 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate/cyclohexane (1:9) as eluent which afforded pure 4-amino-2-chloro-6- trifluoromethoxypyridine (45, 0.3 g, 1.4 mmol, 46%) as a yellow oil.1H NMR (CDCl3, 300 MHz): delta = 6.41 (d, J = 1.6 Hz, 1 H), 6.07 (d, J = 1.6 Hz, 1 H),4.30 (bs, 2 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.8 – 13C NMR (CDCl3, 75 MHz): delta = 157.4, 156.7, 149.7, 119.9 (q, J = 260 Hz), 107.6, 96.0. – C6H4ClF3N2O (212): calcd. (%) C 33.90, H 1.90, N 13.18; found C 33.56, H 2.01, N 12.87.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-96-5, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 623585-74-0, Adding some certain compound to certain chemical reactions, such as: 623585-74-0, name is Methyl 2,5-dichloroisonicotinate,molecular formula is C7H5Cl2NO2, 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 623585-74-0.

To a solution of methyl 2,5-dichloroisonicotinate (2.25 g) in THF (50 mL) was added sodium borohydride (0.828 g), ethanol (20 mL) was added dropwise, and the mixture was stirred at 50C for 4 hr. To the reaction mixture was added 1 M aqueous hydrochloric acid solution. The solvent was evaporated under reduced pressure, and the obtained residue was diluted with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.90 g). MS (ESI+) : [M+H]+177.8.

According to the analysis of related databases, 623585-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-35-8 ,Some common heterocyclic compound, 13466-35-8, molecular formula is C5H4ClNO, 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.

To a stirred solution of triphenylphosphine (814 mg, 3.10 mmol) in THF (7 ml) was added DIAD (603 mul, 3.10 mmol) at 0 oC. The mixture was stirred at 0 oC for about 10 min. To this mixture were added 3-chloro-2-hydroxypyridine (321 mg, 2.481 mmol) and tert- butyl 7-hydroxy-4-azaspiro[2.5]octane-4-carboxylate (470 mg, 2.068 mmol). The mixture was slowly warmed up to RT and stirred at RT overnight. The reaction was quenched with the addition of MeOH (~ 2 ml), and the mixture was concentrated and purified by Isco CombiFlash system on silica gel column (ISCO RediSep gold column, 80g) using 0-100%EtOAc/hexane to give the title compound as an oil after concentration. LCMS m/z [M+H]+ 283.13.

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. 13466-35-8, 3-Chloro-2-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CLAUSEN, Dane; FRADERA, Xavier; GUO, Liangqin; HAN, Yongxin; HE, Shuwen; HUANG, Xianhai; KOZLOWSKI, Joseph; LI, Guoqing; LIM, Jongwon; MARTINOT, Theodore, A.; PASTERNAK, Alexander; SCIAMMETTA, Nunzio; VERRAS, Andreas; XIAO, Li; YU, Wensheng; ZHANG, Rui; (146 pag.)WO2020/41100; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 74936-72-4, name is 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3-carboxylic acid (700g, 2.1mol) in methanol (14 L) was added Quinidine (617g, 1.90mol). The mixture was placed at 90C under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6 %.

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, 74936-72-4, 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1138444-17-3 ,Some common heterocyclic compound, 1138444-17-3, molecular formula is C5H2BrClIN, 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.

6-Bromo-2-chloro-3-iodopyridine (1.50 g, 4.71 mmol) was dissolved in THF (15 mL) and cooled to -78 C, followed by addition of isopropylmagnesium chloride-lithium chloride complex (3.99 mL, 5.18 mmol). The mixture was stirred at -78C for 1 h. 2- (benzyloxy)acetaldehyde (0.849 g, 5.65 mmol) was added and the resulting mixture warmed to 0C and stirred for 2 h. The mixture was treated with saturated NH4C1 and extracted with ethylacetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to gave 2-(benzyloxy)-1-(6-bromo-2-chloropyridin-3-yl)ethanol (1.54g, yield: 95%). MS (M+H): 344.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1138444-17-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]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, SDS of cas: 92276-38-5, blongs to pyridine-derivatives compound. SDS of cas: 92276-38-5

To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 955372-86-8, Adding some certain compound to certain chemical reactions, such as: 955372-86-8, name is 3-Bromo-5-fluoroisonicotinic acid,molecular formula is C6H3BrFNO2, 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 955372-86-8.

A mixture of 3-bromo-5-fluoroisonicotinic acid (5a, 1 .87 g, 8.5 mmol) and HATU (4.85 g, 12.75 mmol) in DMF (30 ml) was added DIEA (4.5 ml), the mixture was stirred at r.t for 20 minutes, then isonicotinimidamide (1 .236 g, 10.2 mmol) was added. Stirring was continued for another 15 hours at r.t. The reaction mixture was concentrated under reduced pressure. The light brown syrup crude mixture was then dissolved in DCM and purified by silica gel chromatography (eluted with 0-10% MeOH/solvent A, solvent A is mixture of 4 liter DCM and 8 ml of 7N ammonia solution in MeOH), fractions 66-80 were pooled and concentrated to afford the desired product 3-bromo-5-fluoro-N-(imino(pyridin-4- yl)methyl)isonicotinamide 5b (566 mg, 20.6%). 1 H NMR (500 MHz, DMSO-d6) delta 10.27 (s, 1 H), 10.09 (s, 1 H), 8.79 – 8.73 (m, 2H), 8.71 (s, 2H), 7.95 – 7.89 (m, 2H). LCMS (m/z [M+H]+): 323.0.

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. 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; BERENSHTEYN, Frada; HAO, Xueshi; HOFFMAN, Timothy; JIN, Qihui; LACOSTE, Arnaud; LEE, Cameron; LIU, Jun; LIU, Yahu; MAIBAUM, Juergen Klaus; MO, Tingting; PAN, Jianfeng; QU, Xin; TCHORZ, Jan; XIE, Yun Feng; YAN, Shanshan; ZOU, Yefen; (564 pag.)WO2018/198077; (2018); A2;,
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.76005-99-7, name is 2-Methoxy-4-methylpyridin-3-amine, molecular formula is C7H10N2O, molecular weight is 138.1671, as common compound, the synthetic route is as follows.Recommanded Product: 2-Methoxy-4-methylpyridin-3-amine

(2) 29.4 g of Compound 2 was dissolved in 600 mL of DCM in a 2 L three-necked flask, and 25.0 g of AcOK potassium acetate was added at 0 C., and 43.4 g of Ac2O; about 40min drops completed, adding 11.25g18-crown ether, maintaining the temperature 0 C, 54.9g of isoamyl nitrite is dripped, about 40min drops completed, the natural return to room temperature.After the system has returned to room temperature, it is heated to 65 degrees reflux overnight (about 12 hours).The next day the TLC test material disappeared, NaHCO3The saturated solution was adjusted to pH = 6, the organic phase was separated, the aqueous phase was extracted once with DCM, the organic phases were combined and dried to dryness, then K2CO3The residue was spin-dried with methanol for about 1 h, filtered and spun dry. The dried residue was then treated with EA and saturated brine. The organic phase was dried to give compound 3 (crude) 29 g, 91.3% yield, which was used directly in Next step.TLC information: Raw Rf = 0.8, Product Rf = 0.5.Developing agent: PE: EA = 1: 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76005-99-7, 2-Methoxy-4-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Si Fenke Si Pharmaceutical Research And Development (Tianjin) Co., Ltd.; Yao Qingjia; Wu Simin; Xu Yangjun; (7 pag.)CN104230811; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55404-31-4 , The common heterocyclic compound, 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, 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.

Step 3: In a sealed tube, NaOMe (25% in MeOH, 3.1 mL, 13 mmol) was added to a solution of compound 94 (1.8 g, 8.7 mmol) in MeOH (17 mL). The reaction was heated at 75 C for 3 days. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with saturated NH4CI and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography over silica gel, which was eluted with heptanes/EtOAc (0-15%) to afford compound 95 as a clear oil (991 mg, 56% yield). 1H NMR (400 MHz, DMSO-c/6) delta 8.00 (d, J = 5.0 Hz, 1 H), 6.98 (d, J = 4.8 Hz, 1 H), 3.90 (s, 3 H), 2.35 (s, 3 H).

The synthetic route of 55404-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 936342-91-5, 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. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, molecular formula is C6H6BrCl2N, 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.

A mixture of 5-bromo-2-methylpyridine (500mg, 2.06mmol) and 1-methanesulfonyl-piperazine (440mg, 2.68mmol) was dissolved in N, N- dimethylformamide (10ml) was then added carbonate potassium (996mg, 7.21mmol), the reaction was stirred for 12 hours at room temperature, 100ml of water was added to the reaction mixture was cooled, (100ml * 3) and extracted with ethyl acetate, then with saturated sodium chloride solution (100ml * 2) and washed to give the organic phase was dried over anhydrous magnesium sulfate filtered, and concentrated under reduced pressure to give 1- (5-bromo – 2-methyl-pyridin) yl-4-methanesulfonyl – piperazine (520mg, white solid), yield: 75.6percent.

According to the analysis of related databases, 936342-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO., LTD; An, Xiaoxia; Bie, Pingyan; Liu, Jun; Yang, Wuli; (42 pag.)CN103360407; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem