Month: April 2022

Electric Literature of 51173-05-8, Adding some certain compound to certain chemical reactions, such as: 51173-05-8, name is 5-Fluoro-2-hydroxypyridine,molecular formula is C5H4FNO, 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 51173-05-8.

To a solution of 5-fluoro-2-hydroxypyridine (200 mg, 1.77 mmol) in concentrated sulfuric acid (900 mul) was added, dropwise over 15 minutes, a premixed solution of concentrated sulfuric acid (900 mul) and fuming nitric acid (170 mul). The internal temperature rose by up to 280C. The reaction mixture was then heated at 650C for 2.5 hours. The cooled mixture was poured onto ice-water, and the pH of the mixture was adjusted to 2.5 with sodium carbonate. It was then extracted with ethyl acetate (2 x 25 ml). The aqueous layer was concentrated and extracted again with a mixture of tetrahydrofuran (25 ml) and ethyl acetate (25 ml). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title compound (112 mg, 40%) as a solid. 1H NMR (400MHz, DMSO-D6): delta 8.22 (dd, 1 H), 8.60 (dd, 1 H); LRMS APCI” m/z 157 [M-H]’.

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2006/114706; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188637-63-0, 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. 188637-63-0, name is (6-Bromopyridin-2-yl)methanamine, molecular formula is C6H7BrN2, 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.

To the mixture of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (233 mg, 1.0 mmol), (6-bromopyridin-2-yl)methanamine (205 mg, 1.1 mmol) in CH3CN (10.0 mL), EDCI (1.3 eq) was added, followed by dropwise addition of DIEA (4.0 eq) at room temperature. The mixture was stirred for 3 h at room temperature and the volatiles are evaporated. The residue was diluted with 50 mL of 10% sodium carbonate and extracted with ethyl acetate. The combined organic solution was successively washed with water, brine and dried over MgSO4. The solution was filtered and the solvent was removed. The residue was purified to afford 101 mg of the title compound.

According to the analysis of related databases, 188637-63-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68175-07-5, Adding some certain compound to certain chemical reactions, such as: 68175-07-5, name is 2-Methyl-1H-imidazo[4,5-b]pyridine,molecular formula is C7H7N3, 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 68175-07-5.

Charged imidazopyridines (XI or XII) (5.115 mmoles), 2-bromo-thiophene-2-carboxamide (VIII) (3.938 mmoles), cesium carbonate (7.161 mmoles), cuprous oxide (0.307 mmoles), 4,7-dimethoxy-l,10-phenathroline (0.716 mmoles), PEG (5.1 15 mmoles) and DMSO to the RB flask fitted with thermo well and condenser. The reaction mass was heated to 110- 1 15 C under magnetic stirring for 24 hours. After completion, it was cooled to room temperature, dichloromethane (500 ml) added and filtered through a celite bed, washed the bed with dichloromethane (100 ml X 2), distilled off the solvent completely under reduced pressure. Aq. ammonia (10 ml) was added and extracted with ethyl acetate (250 ml X 3). Dry the ethyl acetate layer with sodium sulfate, distilled completely to get the crude compound. The crude compound is then purified by using silica gel 60-120 mesh column chromatography and DCM: MeOH 100-5 percent as mobile phase and further by preparative HPLC method to get the pure compounds (XIII, XIV).

According to the analysis of related databases, 68175-07-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; GENZYME CORPORATION; WO2009/137081; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 175204-80-5 ,Some common heterocyclic compound, 175204-80-5, molecular formula is C6H5F3N2, 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 of 4-(trifluoromethyl)pyridin-3-amine (880 mg, 5.40 mmol) in 50% H2S04 (12.25 mL) is cooled to -5 C and a solution of NaN02 (447 mg, 6.48 mmol) in water (4.4 mL) is added slowly. The mixture is left to return to RT and stirring is continued for 30 min. The reaction mixture is heated to 100-110 C for 2 h. The reaction medium is added dropwise to a sat. aq. NaHC03 solution (keep pH > 7), and the mixture is extracted with Et20 (2x) and EtOAc (3x). The organic phases are combined, washed with brine, dried over Na2S0 , filtered and concentrated under reduced pressure to provide hydroxypyridine 31 a1.

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. 175204-80-5, 3-Amino-4-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; STAMMERS, Timothy; BARBEAU, Xavier; BEAULIEU, Pierre; BERTRAND-LAPERLE, Megan; BROCHU, Christian; EDWARDS, Paul, J.; FORGIONE, Pasquale; GODBOUT, Cedrickx; HUCKE, Oliver; JOLY, Marc-Andre; LANDRY, Serge; LEPAGE, Olivier; NAUD, Julie; PESANT, Marc; POIRIER, Martin; POIRIER, Maude; THAVONEKHAM, Bounkham; WO2011/32277; (2011); 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. 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., SDS of cas: 63572-73-6

10 % Palladium on carbon (40 mg) was added to a solution of 5-nitro-1H-pyrazolo[3,4-b]pyridine (A) (308 mg, 1.876 mmol) in ethanol and tetrahydrofuran and the mixture was charged with H2 (gas). After stirring the reaction mixture for 15 h, the mixture was filtered using celite and purified by column chromatography. The desired product 1H-pyrazolo[3,4-b]pyridin-5-amine (B) (73 mg) was obtained as 89 % yield.

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, 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13816; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 298709-29-2, 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.298709-29-2, name is 3,5-Difluoropicolinonitrile, molecular formula is C6H2F2N2, molecular weight is 140.0903, as common compound, the synthetic route is as follows.

A solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -78C. 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 -4C. 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 00C for 30 minutes and room temperature for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aqueous phase was neutralized to pH 9 with NaHCO3 and extracted with EtOAc (2 X 20 ml). The organic layers were combined and the volatiles were removed under reduced pressure. Purification by ISCO (0-10% EtOAc- hexanes) gave the title product as light yellow oil. LCMS: 158 [M+H]

The chemical industry reduces the impact on the environment during synthesis 298709-29-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/150462; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1256810-26-0 ,Some common heterocyclic compound, 1256810-26-0, molecular formula is C7H6BrNO3, 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 mixture of 6-bromo-3-methoxypicolinic acid (1.84 g, 7.93 mmol) and 3- fluorobenzene-l,2-diamine (1.0 g, 7.93 mmol) was stirred in PPA (3 mL) on a pre-heated oil- bath at 120 C for 14 h. The mixture was poured to ice-water and basified to pH = 8 with Na2C03. Then the mixture was filtrated to collect the brown solid as 6-bromo-2-(4-fluoro-lH- benzo[d]imidazol-2-yl)pyridin-3-ol (900 mg, yield: 37%). The filtrated was extracted with ethyl acetate, and the organic layer was washed with brine and dried over Na2S04. After concentrated, the residue was purified by column chromatography to give the product of 2-(6-bromo-3- methoxypyridin-2-yl)-4-fluoro-lH-benzo[d] imidazole (350 mg, yield: 14%). 1H- MR (CDC13, 400 MHz) delta 10.43-10.56 (m, 1H), 7.46 (d, J= 8.8 Hz, 1H), 7.33 (d, J= 8.8 Hz, 1H), 7.21-7.30 (m, 2H), 6.90-6.98 (m, 1H), 4.05 (s, 3H). MS (M+H) : 322 / 324.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256810-26-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HE, Shuwen; DAI, Xing; PALANI, Anandan; NARGUND, Ravi; LAI, Zhong; ZORN, Nicolas; XIAO, Dong; DANG, Qun; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/121418; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 81803-60-3 ,Some common heterocyclic compound, 81803-60-3, molecular formula is C10H10N2O2, 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 an ice cold solution of ethyl imidazo[l,5-alpha]pyridine-3-carboxylate (10 g, 52.6 mmol) in acetonitrile (500 mL) was added N-bromo succinimide (9.36 g, 52.6 mmol). The mixture was allowed to stir for 1 h at which time triethylamine (10 mL) was added to the deep red- violet solution. The color dissipated and the solution was concentrated. Purification of the crude solid by silica gel chromatography (0-20% EtOAc/Hexanes) provided a white crystalline solid (13.5 g 95%). MS 268.9 (M + 1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81803-60-3, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/85302; (2008); A1;,
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 77618-99-6, name is 2-Amino-5-(methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Amino-5-(methylthio)pyridine

Step 2: 4-Chloro-7-[5-(methylthio)-2-pyridinyl]-6,7-dihydro-5H-pyrrolo[2,3- cflpyrimidine (200)To a stirred solution of (4,6-dichloro-5-pyrimidinyl)acetaldehyde 209 (see example 116, step 1 , 3.41 g, 17.8 mmol) in MeOH (180 mL) was added 199 (3.0 g, 21.4 mmol) at RT. The reaction mixture was cooled to -15 0C with an ice/methanol bath and glacial acetic acid (3.1 mL, 53.4 mmol) and NaBH3CN (3.35 g, 53.4 mmol) were added. The reaction mixture was stirred at -15 0C for 15 min then allowed to warm to RT and stir for 19 h. The reaction mixture was then diluted with water (50 mL) and extracted with CH2CI2 (3 x 100 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a yellow oil. The crude oil was dissolved in THF (500 mL) with stirring and then f-BuOK (5.99 g, 53.4 mmol) was added in one portion at RT. The reaction mixture changed immediately to a brown color and was stirred at RT for 22 h. The reaction mixture was quenched with water (50 mL), concentrated under reduced pressure, and then redissolved in EtOAc (200 mL). The organic layer was washed with water (1 x 50 mL) and the aqueous layer was extracted with EtOAc (2 x 100 ml_). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a brown oil. The crude oil was purified using SiO2 flash chromatography (20% to 40% EtOAc in hexanes; monitored at 319 nm) to give 550 mg (1 1%) of the title product 200 as a colorless oil. 1H NMR (400 MHz, CDCI3): delta 8.57 (d, J = 9.0 Hz, 1 H), 8.43 (s, 1 H), 8.29 (d, J = 2.4 Hz, 1 H), 7.68 and 7.66 (dd, J1 = 8.8 Hz, J2 = 2.4 Hz, 1 H), 4.37 – 4.33 (m, 2 H), 3.16 (t, J = 8.8 Hz, 2 H), 2.47 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 77618-99-6.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
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 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Bromo-5-nitropyridin-4-amine

Synthesis of 323-1. To a mixture of 323-0 (1.00 g, 4.6 mmol), 4-fluorophenylboronic acid (773 mg, 5.5 mmol) and Cs2CO3 (3.00 g, 9.2 mmol) in dioxane/H2O (20 mL/4 mL) was added Pd(PPh3)4 (531 mg, 0.5 mmol) under N2 atmosphere. The mixture was stirred at 95 C for 2 hours and then concentrated in vacuo. The residue was dissolved with EtOAc (60 mL) and the resulting solution was washed with brine (20 mL × 3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 50 : 1) to give 323-1 (1.00 g, 93 %) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 84487-15-0.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem