Day: May 14, 2021

Synthetic Route of 1060812-84-1 ,Some common heterocyclic compound, 1060812-84-1, molecular formula is C7H5BrN2, 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.

A solution mixture of 5-bromopyrazolo[1 ,5-a]pyridine 94-2 (900 mg, 4.59 mmol) and tBuONa (661 .2 mg, 6.88 mmol) in toluene (10 mL) was degassed with argon for about 10 mm. To this mixture were added Pd2(dba)3 (84 mg, 0.091 mmol), BINAP (114.2 mg, 0.lO2mmol) and cyclopropylamine (2 mL, 28.87 mmol) under argon atmosphere. The resulting reaction mixture was maintained at 90C for 2 h under microwave irradiation. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was washed with water (30 mL), brine (25 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography over silica-gel (100-200 mesh) using a solvent gradient of 25% ethyl acetate in pet-ether to afford 500 mg (62%) of N-cyclopropylpyrazolo[1,5-a]pyridin-5- amine 147-1 as a brown solid. 1H-NMR (400 MHz, CDCI3): c58.18 (d, J= 7.5 Hz, 1H), 7.78 (d, J= 2.2 Hz, 1H), 6.72 (d, J= 2.6 Hz, 1H), 6.15-6.18 (m, 2H), 4.28 (5, 1H), 2.44-2.49 (m, 1 H), 0.78-0.80 (m, 2H), 0.54-0.58 (m, 1 H). ESI-LC/MS: m/z 173.75 (M+H); R =1 .99 mm [Waters Acquity UPLC with Quattro-micro detector; Waters Acquity BEH Cl 8,1.7 pm, 2.1 X 50 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) hold for 0.5 mm and to 10:90 H20 (0.025% TEA):CH3CN (0.025% TEA) in 3.5 mm and hold for 1 .5 mm with flow rate of 0.4 mLlmin].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060812-84-1, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); 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.10177-29-4, name is 4-Chloronicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.5545, as common compound, the synthetic route is as follows.Recommanded Product: 4-Chloronicotinic acid

A mixture of amine 4 (1eq.), carboxylic acid (1.2 eq.), diisopropylethylamine (DIEA) (1.5 eq.), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimidehydrogen chloride (EDC·HCl) (1.2 eq.) in dichloromethane was stirred at room temperature for18 h. The reaction mixture was diluted with dichloromethane and washed withwater and brine. The organic layer was dried over MgSO4 andconcentrated. The crude product was purified by normal phase column chromatography(SP1, Biotage) to yield compound 5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10177-29-4, 4-Chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Article; Hwang, Jong Yeon; Smithson, David C.; Holbrook, Gloria; Zhu, Fangyi; Connelly, Michele C.; Kaiser, Marcel; Brun, Reto; Kiplin Guy; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4127 – 4131;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1017789-38-6, name is tert-Butyl (4,6-dichloropyridin-2-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H12Cl2N2O2

1017789-38-6) (200 mg, 0.760 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (348 mg, 1.67 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.076 mmol), and potassium phosphate tribasic (484 mg, 2.28 mmol) in a flask was evacuated and backfilled with argon three times. Dioxane (3 mL) and water (0.33 mL) were added, and the reaction mixture was heated to 100C for 5 hours. The mixture was allowed to cool to room temperature. Hydrochloric acid (4.0 N in dioxane, 3.80 mL, 15 mmol) was added to the mixture, and the suspension was stirred vigorously for 14 hours at room temperature. The mixture was filtered and concentrated under reduced pressure. The residue was dissolved in DMSO and purified via reverse phase HPLC (15-50% acetonitrile/water with 0.1% TFA, linear gradient) to give 4,6-bis(l -methyl- lH-pyrazol-4-yl)pyridin-2-amine. MS ESI calc’d. for C13H15N6 [M + H]+ 255, found 255. 1H NMR (500 MHz, DMSO-d6) delta 8.46 (s, 1H), 8.42 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70-7.59 (m, 2H), 7.40 (s, 1H), 6.80 (s, 1H), 3.93 (s, 3H), 3.90 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1017789-38-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DONOFRIO, Anthony; ELLIS, John Michael; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; WO2013/52393; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22245-83-6, 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 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 117 5-nitro-3-(trifluoromethyl)pyridin-2-ol; 2-Hydroxy-3-(trifluoromethyl)pyridine (3.0 g) was added to conc. sulfuric acid (18 mL) under ice-cooling, and the mixture was stirred at the same temperature for 5 min. Fuming nitric acid (90-95%, 7 mL) was added dropwise over 5 min, and the mixture was allowed to return to room temperature over 2 hr, heated to 50 C. and stirred for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice (200 g), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was washed with diisopropyl ether to give the title compound as a solid (yield 2.7 g, 69%). 1H-NMR (CDCl3) delta: 8.65-8.67 (1H, m), 8.80-8.81 (1H, m), 1H not detected.

According to the analysis of related databases, 22245-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5398-44-7, 2,6-Dichloroisonicotinic acid, 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, 5398-44-7, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of 2,6-dichloroisonicotinic acid (10.0 g, 52.1 mmol) in THF (213 mL) at 0 0C was added dimethylaminopyridine (3.18 g, 26.0 mmol). A solution of di-tert-butyl dicarbonate (13.64 g. 62.5 mmol) in THF (20 mL) was added and the mixture was allowed to warm to ambient temperature. After 18 h, the solvent was removed and HCl (0.1 Nu aqueous solution) was added and the mixture was extracted with ethyl acetate (3x). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated: LC-MS [M+l-16] = 233.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5398-44-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BURGEY, Christopher, S.; DENG, Zhengwu, J.; NGUYEN, Diem, N.; PAONE, Daniel, V.; POTTEIGER, Craig, M.; STAUFFER, Shaun, R.; SEGERDELL, Carolyn; NOMLAND, Ashley; LIM, John, J.; WO2010/111058; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56026-36-9, 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.56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate, molecular formula is C8H9NO3, molecular weight is 167.16, as common compound, the synthetic route is as follows.

Dess-Martin periodinane (3.0 g, 7.2 mmol) was added slowly to the mixture of compound 38 (1.0 g,6.0 mmol) in DCM (10 mL). The resulting mixture continued to stir at room temperature overnight.The reaction was quenched with water. The aqueous phase was extracted with EtOAc. The combinedorganic phases were then processed in the usual way and chromatographed (3:1 petroleum ether/EtOAc)to yield compound 39 (0.85 g, 86%).

The chemical industry reduces the impact on the environment during synthesis 56026-36-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Wen-Long; Yang, Dong-Lin; Gao, Li-Xin; Tang, Chun-Lan; Ma, Wei-Ping; Ye, Hui-Hua; Zhang, Si-Qi; Zhao, Ya-Nan; Xu, Hao-Jie; Hu, Zhao; Chen, Xia; Fan, Wen-Hua; Chen, Hai-Jun; Li, Jing-Ya; Nan, Fa-Jun; Li, Jia; Feng, Bainian; Molecules; vol. 19; 1; (2014); p. 102 – 121;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54415-77-9, Adding some certain compound to certain chemical reactions, such as: 54415-77-9, name is 1H-Pyrrolo[3,2-c]pyridin-4(5H)-one,molecular formula is C7H6N2O, 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 54415-77-9.

General procedure: A solution of 6,7-dimethoxyisoquinolin-1(2H)-one(200 mg, 0.97 mmol), phosphoryl trichloride (0.268 mL, 2.92 mmol) inacetonitrile (5 mL) was stirred at 110 C for 5 minutes under microwaveirradiation. The reaction was quenched with a saturated aqueous sodium bicarbonatesolution and stirred at ambient temperature for 1 h. It was filtered throughcelite and washed with ethyl acetate. The filtrate was concentrated to dryness.The crude material was purified by flash chromatography, eluting with heptanesand ethyl acetate (1:0 to 0:1) to give the desired product as a gum (99 mg,45.4 %).

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. 54415-77-9, 1H-Pyrrolo[3,2-c]pyridin-4(5H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Yun-Jin; St.-Onge, Miguel; Laliberte, Sebastien; Vallee, Frederic; Jin, Shujuan; Bedard, Leanne; Labrecque, Jean; Albert, Jeffrey S.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 14; (2014); p. 3199 – 3203;,
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, 31181-79-0, blongs to pyridine-derivatives compound. Formula: C6H6FNO

To a solution of (3-fluoropyridin-2-yl)methanol (1.80 g, 13.8 mmol, 1.0 equiv) in DCM (20 mL) was added SOCI2 (2.50 mL, 35.0 mmol, 2.5 equiv) dropwise at 0C. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated aqueous NaHCCb solution and extracted with DCM (3 * 20 mL). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column chromatography (eluted with PE/EtOAc = 5/1) to afford 2-(chloromethyl)-3-fluoropyridine (1.33 g, 66% yield). LC-MS: m/z 146.0, 148.0 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31181-79-0, its application will become more common.

Reference:
Patent; ANNAPURNA BIO, INC.; TANG, Haifeng; HANSON, Michael; BOYCE, Sarah; NIE, Zhe; (461 pag.)WO2020/73011; (2020); 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.13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.COA of Formula: C5H4BrNO

To a solution of N-(4-(4-hydroxy-2,6-dimethylphenyl)-thiazol-2-yl)isonicotinamide (5-3, 325 mg, 1.0 mmol) in DMF (15 mL) were added cesium carbonate (650 mg, 2.0 mmol, 2.0 equiv) and Cu (19.5 mg, 0.30 mmol, 0.30 equiv). The mixture was stirred at 80-90 C for 60 min 5-Bromo-2-hydroxypyridine (261 mg, 1.5 mmol) was added to the solutionand the reaction mixture was stirred at 100 C for additional 24 hr. The solution was quenched with water (40 mL) and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on (NH silica gel, hexane/ethyl acetate = 3/1-1/3) to give 5(0.75 g) in 18% yield: 1H NMR (500 MHz, CDCl3) delta 8.31 (d, J= 5.0 Hz, 2 H), 8.29 (d, J= 5.0 Hz, 2 H), 7.23 (d, J= 9.5 Hz, 1 H), 6.81 (s, 1H), 6.60 (d, J= 4.76 Hz, 1 H), 6.49 (s, 2 H), 5.42 (s, 1 H), 2.04 (s, 6 H), ESI-MS = m/z 417.2 (M – H)-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13466-38-1, 5-Bromopyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; TAIVEX THERAPEUTICS CORPORATION; HUANG, Yu-Ling; CHUANG, Shih-Hsien; LEE, Ying-Shuan Eda; HUANG, Jiann-Jyh; LAU, Johnson; WO2013/82324; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 125652-55-3, 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.125652-55-3, name is 1-Butyl-3-methylpyridinium Chloride, molecular formula is C10H16ClN, molecular weight is 185.69, as common compound, the synthetic route is as follows.

Example 91-Butyl-3-methylpyridinium dicyanodihydridoborate-[BMPy][BH2(CN)2]4.09 g (46.6 mmol) of sodium dicyanodihydridoborate, Na[BH2(CN)2], and 8.63 g (46.5 mmol) of 1-butyl-3-methylpyridinium chloride, [BMPy]Cl, are each dissolved in 20 ml of water and mixed. The product, 1-butyl-3-methylpyridinium dicyanodihydridoborate, [BMPy][BH2(CN)2], is extracted with 100+100+50 ml of CH2Cl2. The combined organic phases are washed with 50+50 ml of water, dried using Na2SO4, and the solvent is distilled off. [BMPy][BH2(CN)2] is dried at about 40 C. in vacuo for one day with stirring. The yield of 1-butyl-3-methylpyridinium dicyanodihydridoborate is 9.0 g (41.8 mol, 90%). 1H{11B}-NMR (solvent: acetone-D6; reference: TMS): delta, ppm=0.97 t (CH3, 3H), 3JH,H=7.5 Hz; 1.02 s (2H, BH2); 1.44 m (CH2, 2H); 2.08 m (CH2, 2H); 2.63 s (CH3, 3H), 4.71 t (CH2, 2H), 3JH,H=7.6 Hz; 8.08 d, d (CH, 1H), 3JH,H=7.0 Hz; 8.50 d (CH, 1H), 3JH,H=8.1 Hz; 8.88 d (CH, 1H), 3JH,H=6.1 Hz; 8.95 s (CH, 1H). 11B{1H}NMR (solvent: acetone-D6; reference: Et2O.BF3): delta, ppm=-41.7 s

The chemical industry reduces the impact on the environment during synthesis 125652-55-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Patent GmbH; Ignatyev, Nikolai (Mykola); Schulte, Michael; Bernhardt, Eduard; Bernhardt-Pitchougina, Vera; Willner, Helge; US8927714; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem