Day: March 18, 2022

Reference of 109306-86-7 , The common heterocyclic compound, 109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

2- (2-bromophenyl) pyridine(40.7 g, 174.0 mmol) was dissolved in 500 ml of anhydrous THF and cooled to -78 C. 2.5 M n-BuLi (73.2 ml, 183 mmol) was slowly added thereto and stirred for 1 hour.To this reaction solution was added 9-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] dioxin-11-one (53.0 g, 165.4 mmol) obtained in the above Step 3 The temperature was then slowly raised to room temperature and stirred for 3 hours.Aqueous ammonium chloride solution was added to terminate the reaction, distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure and then purified by column chromatography to obtain the compound 9-chloro-11- (2- (pyridin-2-yl) phenyl) -11H-indeno [ Benzo [b, e] [1,4] dioxin-11-ol (69.6 g, yield 80%).

The synthetic route of 109306-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doosan Co., Ltd; Choi Tae-jin; Kim Yeong-bae; Kim Hoe-mun; (65 pag.)KR2019/30391; (2019); 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. 188577-69-7, name is 3,4-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 188577-69-7

3,4-dichloro-2-aminopyridine (500 mg, 3.07 mmol, prepared with reference to document: Synthetic Communications, 1997, 27(5), 861-870.) and 2-fluoro-4-nitrophenol (1.928 g, 12.27 mmol) were heated to 120 C. and melted, and stirred for 24 hrs. The molten was cooled to room temperature, and subjected to silica gel column chromatography (the eluent was dichloromethane to dichloromethane/methanol=50/1) for purification, to obtain a white solid (137 mg, 16%). 1H NMR (DMSO-d6, 300 MHz) delta 8.38 (dd, 1H, J=10.5, 2.4 Hz), 8.148.09 (m, 1H), 7.86 (d, 1H, J=5.4 Hz), 7.427.36 (m, 1H), 6.60 (br, 2H), 6.27 (d, 1H, J=5.4 Hz).

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, 188577-69-7, 3,4-Dichloropyridin-2-amine.

Reference:
Patent; SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY CO., LTD; Cheng, Jianjun; Qin, Jihong; Ye, Bin; US2014/206679; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63237-88-7, 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Preparation 99Methyl 6- r(1 RV1 -(4-fluorophenvnethyll(pyrazolori ,5-alpyridin-2- ylcarbonyl)amino}methyl)pyridine-2-carboxylate To a stirred solution of the amine from Preparation 20 (49mg, 0.17mmol) in dichloromethane (1 ml_) was added pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27.6mg, 0.17mmol) followed by N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (32.6mg, 0.17mmol) and the reaction mixture was stirred for 23 hours. Saturated aqueous NaHC03 solution (2ml_) was added and the mixture was stirred vigorously for 10 minutes before filtering through a phase separation cartridge. The solvent was removed in vacuo and the residue purified by column chromatography (silica 50-100% ethyl acetate in pentane as eluent). The solvent was removed in vacuo to give the title compound as a clear gum (37mg, 50%). 1 H NMR (400 MHz, CDCI3): the compound appears to exist as two non-interconverting rotameric forms in CDCI3 in the ratio ca. 2:1. Data for these rotamers are listed separately.Major: delta ppm: 1.62 (d, 3H), 3.99 (s, 3H), 4.56 (d, 1 H), 4.94 (d, 1 H), 6.21 -6.35 (m, 1 H), 6.82-6.99 (m, 4H), 7.17 (t, 1 H), 7.28-7.39 (m, 2H), 7.50 (d, 1 H), 7.59 (d, 1 H), 7.70 (t, 1 H), 7.92 (d, 1 H), 8.47 (d, 1 H).Minor: delta ppm: 1.56 (d, 3H), 3.99 (s, 3H), 5.05 (d, 1 H), 5.31 (d, 1 H), 6.21 -6.35 (m, 1 H), 6.72 (t, 1 H), 6.82-6.99 (m, 3H), 7.08 (t, 1 H), 7.28-7.39 (m, 3H), 7.50 (d, 1 H), 7.58 (d, 1 H), 7.86 (d, 1 H), 8.16 (d, 1 H).LRMS (ESI) m/z 433 [MH]+

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; GLOSSOP, Paul Alan; PALMER, Michael John; ANDREWS, Mark David; WO2012/120398; (2012); 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. 89415-54-3, name is 5-Bromo-N2-methylpyridine-2,3-diamine, the common compound, a new synthetic route is introduced below. Formula: C6H8BrN3

A solution of 5-bromo-N*2*-methylpyridine-2,3-diamine (Stage 67.1.4, 960 mg, 4 75 mmo.) and tetramethyl orthocarbonate (Aki?ch, Buchs, Switzerland, 2 ml, 14 7 mmol) and acetic acid (0 273 ml, 4 75 mmol) was stirred for 90 min at 100 C The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine The aqueous layer was extracted with EtOAc and the combined organic layers washed with saturated aqueous NaHCO3 and with brine, then dried over Na2SO4, filtered and evaprated The crude product was dry loaded on silica gel and purifted by MPLC (DCM/MeOH 0% – 4%) to g>;ve the title compound as a green solid. (HPLC tR 2.83 mm (Method A), M+H – 242, 244 MS-ES).

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 960289-03-6, 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.960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, molecular weight is 232.1, as common compound, the synthetic route is as follows.

Preparation 22; 2-(4-Fluoro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridine-7-one; Add tetrakis(triphenylphosphine) palladium(O) (0.075g, 0.065 mmol) to a degassed solution of 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.5 g, 2.15 mmol), 4-fluorophenylboronic acid (0.30 g, 2.15 mmol), and sodium carbonate (0.46 g, 4.30 mmol) in N,N-dimethylformamide (21 mL), methanol (5 mL) and water (1 mL). Heat the reaction at 90 0C for 16 h. Allow the reaction to cool to RT and pour into water (75 mL). Filter the resulting solid and dry in vacuo at 80 0C to give 0.40 g (75%) of the title compound. MS/ES m/z 248.0 [M+H]+ .

The chemical industry reduces the impact on the environment during synthesis 960289-03-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 872355-63-0, 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.872355-63-0, name is Methyl 1H-pyrrolo[3,2-b]pyridine-5-carboxylate, molecular formula is C9H8N2O2, molecular weight is 176.172, as common compound, the synthetic route is as follows.

A solution of methyl 1 H-pyrrolo[3,2-b]pyridine-5-carboxylate (Adesis Inc., New Castle, Delaware) (1.0 g, 5.68 mmol) and di-te/t-butyl dicarbonate (1.75 g, 7.95 mmol) in methanol (30 ml.) was passed through an H-cube hydrogenation apparatus equipped with a 10%Pd/C cartrige at 80 degrees Celsius and 80 bar 1.0 mL/minute. The effluent was then passed through the H-cube apparatus three additional times. The crude material was concentrated and the residue was purified by silica gel chromatography, eluting with a gradient mixture of 50% to 90% ethyl acetate to heptane to give 230 mg of methyl 2,3-dihydro-1 H-pyrrolo[3,2-b]pyridine-5-carboxylate and 300 mg of 1-te/t-butyl 5- methyl 2,3-dihydro-1 H-pyrrolo[3,2-b]pyridine-1 ,5-dicarboxylate.Methyl 2,3-dihydro-1 H-pyrrolo[3,2-b]pyridine-5-carboxylate:_1H NMR(deuterochloroform) delta 7.77 (d, J = 8.2 Hz, 1 H), 6.67 (d, J = 8.2 Hz, 1 H), 4.42 (br. s., 1 H), 3.88 (s, 3H), 3.69 (td, J = 8.6, 1.5 Hz, 2H), 3.17 (t, J = 8.7 Hz, 2H).1-te/t-Butyl 5-methyl 2,3-dihydro-1 H-pyrrolo[3,2-b]pyridine-1 ,5-dicarboxylate: 1H NMR (deuteurochloroform) delta 7.92 (d, J = 8.2 Hz, 2H), 4.00 (t, J = 8.9 Hz, 2H), 3.91 (s, 3H), 3.25 (t, J = 1.0 Hz, 2H), 1.52 (br. s., 9H).

The chemical industry reduces the impact on the environment during synthesis 872355-63-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 912934-77-1, Adding some certain compound to certain chemical reactions, such as: 912934-77-1, name is 6-Bromopyridine-2-sulfonyl chloride,molecular formula is C5H3BrClNO2S, 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 912934-77-1.

To a solution of compound from Example 1 step e (142 mg, 0.5 mmol) in pyridine (2 mL) was added 6-bromopyridine-2-sulfonyl chloride (128 mg, 0.5 mmol). The mixture was stirred at rt overnight. After evaporated most of the pyridine, the residue was purified by silica gel column chromatography to obtain the desired product (120 mg, 48%) as a pale-yellow foam which will be used directly for the next step.

According to the analysis of related databases, 912934-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; YU, Jianming; SHOOK, Brian, C.; BLAISDELL, Thomas, P.; KIM, In, Jong; PANARESE, Joseph; MCGRATH, Kevin; NEGRETTI-ENMANUELLI, Solymar; OR, Yat, Sun; (301 pag.)WO2017/123884; (2017); 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. 30766-03-1, name is 4-Bromopicolinic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H4BrNO2

Triethylamine (1.05 equiv.) was added to a suspension of 4-bromopicolinic acid in benzole (5 mL/mmol), followed by chloroformate (1.05 equiv.) and the reaction mixture stirred 1 h at RT. Triethylamine hydrochloride was filtered out and the filtrate evaporated to low bulk. The anhydride thus obtained was taken up in THF (5 mL/mmol) and added in drops to a suspension of lithium aluminium hydride (1 equiv.) in THF (2 mL/mmol) at -78 C. The mixture was stirred for 30 min. at -78 C., then sat. Na2SO4 sol. was added, filtered over celite, washed with EE and the organic phase was evaporated to low bulk. The raw product thus obtained was purified by column chromatography (30% EE in hexane) (yield approx. 50%).

The synthetic route of 30766-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; US2009/69320; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 298709-29-2, 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 298709-29-2, name is 3,5-Difluoropicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 33 ; l-(3,5-Difluoropyridin-2-yl)ethanoneA solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -780C. 3,5-difluoropicolinonitrile (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temperature was kept below -40C. After the addition was complete, the reaction mixture was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction mixture was stirred at O0C for 30 minutes and at room temperature for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aquous phase was neutralized to pH9 with NaHCO3 and extracted with EtOAc (2 x 20 ml). The organic layers were combined and the volatiles were removed under reduced pressure. Purification utilizing ISCO (0-10% EtOAc- hexanes) gave the title product as light yellow oil. LC-MS: 158 [M+H]+.

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 298709-29-2, 3,5-Difluoropicolinonitrile.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); 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.22280-56-4, name is 2-Chloro-3-methyl-5-nitropyridine, molecular formula is C6H5ClN2O2, molecular weight is 172.5691, as common compound, the synthetic route is as follows.SDS of cas: 22280-56-4

3-Methyl-5-nitropyridin-2-ol (134 g, 0.872 mol) (J. Org. Chem. 1949, 14, 328-332) was divided into 3 portions and placed in three 1-L round bottom flasks. POCl3 (200 mL) was added to each flask and the mixtures were heated to reflux for 2 h. The solutions were cooled and the excess POCl3 was removed in vacuo. The residues were poured into ice water (1 L) with stirring and the precipitates were collected by filtration and air dried for 20 min. The combined products were recrystallized from 10% ethyl acetate in hexanes (300 mL) and air dried to give 2-chloro-3-methyl-5-nitropyridine (139 g, 92% yield) as a white solid which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) delta 9.04 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.2 Hz, 1H), 2.50 (s, 3H).2-Chloro-3-methyl-5-nitropyridine (139 g, 0.806 mol) from the above procedure was divided into two portions and placed in two 2-L round bottom flasks with methanol (500 mL). The solutions were cooled in dry ice/isopropanol baths as solid sodium methoxide (26.5 g, 0.467 mol) was added portion-wise to each flask so that the temperature was remained below 20 C. When the additions were complete, the resulting mixtures were heated to reflux for 1 h. The mixtures were cooled and diluted with ice water (500 mL) to give white precipitates, which were collected by filtration. The combined filtrates were washed with water and air dried to give 2-methoxy-3-methyl-5-nitropyridine (127 g, 97% yield) as a white solid: 1H NMR (400 MHz, CDCl3) delta 8.91 (d, J=2.0 Hz, 1H), 8.16 (s, 1H), 4.06 (s, 3H), 2.25 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 165.83, 141.91, 139.37, 132.92, 121.77, 54.83, 15.84. An analytical sample was recrystallized from hexane to give white needles, mp 95-96.5 C. Anal. calcd. for C7H8N2O3: C, 50.00, H, 4.79, N, 16.66. Found: C, 49.73, H, 5.02, N, 16.48.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-56-4, 2-Chloro-3-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/29684; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem