Category: pyridine-derivatives

Application of 6854-07-5, 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. 6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid. A new synthetic method of this compound is introduced below.

2-Hydroxy-5-nitronicotinic acid (2.7 mmol) in a mixture of /V,/V-di methyl formamidc (2.7 mmol) and thionyl chloride (5 ml) was heated at 80C for 1 h. The mixture was allowed to cool and concentrated in vacuo. To the resulting residue was added ice- water (20 ml) and with vigorous stirring a precipitate formed. The precipitate was filtered off and dried in a vacuum oven to give a white solid (68%). (0180) ESIMS: M-l: 201. (0181) 9.30 (1H, d, H-4), 8.83 (1H, d, H-6).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; BIONOMICS LIMITED; O’CONNOR, Sue; RATHJEN, Deborah; (55 pag.)WO2019/109150; (2019); 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. 54232-43-8, name is 6-Bromo-5-methoxypicolinic acid. A new synthetic method of this compound is introduced below., HPLC of Formula: C7H6BrNO3

To a solution of 6-bromo-5-methoxy-2-pyridinecarboxylic acid (2d) (12 g, 52 mol) in pyridine (70 mL) was added EDCI (11.5 g, 59 mmol) and cyclopropylmethylamine (3.6 g, 52 mmol). The reaction mixture was stirred at room temperature overnight and then concentrated under vacuum. The reaction mixture was diluted with water (100 mL) and ethyl acetate (100 mL). The organic layer was separated and the water layer was extracted with ethyl acetate (2 x 100 mL). The organic layers were combined and washed with water (2 x 50 mL), brine (500 mL), dried over magnesium sulphate, filtered and concentrated under vacuum to furnish 10.43g of crude product. The crude product was converted into a slurry (silica gel 20 g) and purified by flash column chromatography (silica gel 230 g, eluting with 0-100% ethyl acetate in hexane) to yield compound 6-bromo-N-(cyclopropylmethyl)-5-methoxypicolinamide (2e) (8.02 g, 54%) as off white solid, mp 67-70 C; 1HNMR (300 MHz, DMSO-d6) delta 8.51 (t, J = 5.8, 1 H), 8.02 (d, J = 8.4, 1 H), 7.65 (d, J = 8.5, 1 H), 3.96 (s, 3H), 3.14 (t, J = 6.5, 2H), 1.11 – 0.99 (m, 1 H), 0.47 – 0.36 (m, 2H), 0.27 – 0.20 (m, 2H); MS (ES+) 307.0, 309.0 (100% M+Na)

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, 54232-43-8, 6-Bromo-5-methoxypicolinic acid.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KAMATH, Vivekanand P.; GOWAN, Walter; (222 pag.)WO2016/29214; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 38186-85-5, 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. 38186-85-5, name is 2-Bromo-5-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a solution of 2-bromo-5-fluoro-3-methyl-pyridine (4.90 g) in AcOEt (100 ml) and MeOH (10 ml) was subsequently added NEt3 (5.4 ml) and 1,1 ‘- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct (490 mg) and the mixture was carbonylated at 100 bar CO and 110C for 20 h. The mixture was evaporated and the residue purified by chromatography on silica gel using n- heptane/ AcOEt (7: 1) to give the title compound (3.44 g) as a pale red solid. MS: m/z = 170.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38186-85-5, 2-Bromo-5-fluoro-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A.; BANNER, David; GUBA, Wolfgang; HILPERT, Hans; HUMM, Roland; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; POWER, Eoin; ROGERS-EVANS, Mark; ROMBACH, Didier; WOLTERING, Thomas; WOSTL, Wolfgang; WO2011/138293; (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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, molecular formula is C8H5ClN2O2, 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. Formula: C8H5ClN2O2

To a solution of carboxylic acid 14 in methylene chloride under an atmosphere of nitrogen was added 1.5 equivalents of oxalyl chloride followed by catalytic amount of dimethylformamide. The reaction was stirred for 18 hours before the addition of an excess of methanol. After 2 hours stiffing the reaction was evaporated to dryness to give the title compound 15 as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.87 (s, 3H) 6.62-6.63 (m, 1H) 7.68-7.69 (m, 1H) 8.68-8.70 (m, 1H) 12.37 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 920966-03-6.

Reference:
Patent; Helicon Therapeutics, Inc.; US2012/95016; (2012); 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 75291-85-9, name is 5-Bromo-2-chloronicotinamide. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Bromo-2-chloronicotinamide

Preparation 118tert-butyl (3S,4R)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl-(3S,4R)-3-fluoro-4-hydroxy-piperidine- 1 -carboxylate (WO 20131011402 Al), 3.5 g, 15.98 mmol) in DMSO (20 mL) was added potassium tert-butoxide(2.68 g, 23.97 mmol) and the mixture was stirred at room temperature for 30 minutes. 5-bromo-2-chloropyridine-3-carboxamide (Preparation 177, 2.75 g, 15.98 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction was quenched by the addition of water (20 mL) and extracted into EtOAc (2 x 100 mL). The organic layers were combined, washed with water (2 x 50 mL), dried over sodium sulphate and concentrated in vacuo. Theresidue was purified using silica gel column chromatography eluting with 20% EtOAc inheptanes to afford the title compound (5.00 g, 75%).1H NMR (400 MHz, DMSO-d6): O ppm 1.40 (5, 9H), 1.80-1.86 (m, 1H), 1.92-1.97 (m, 1H), 2.93-3.00 (m, 1H), 3.07-3.12 (m, 1H), 3.90-4.18 (m, 2H), 4.95-5.08 (m, 1H), 5.35-5.43 (m, 1H), 7.52(br 5, 1 H), 7.92 (br 5, 1 H), 8.27 (d, 1 H), 8.43 (d, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 75291-85-9.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); 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. 113209-90-8, name is (4-Chloro-5-fluoropyridin-2-yl)methanol, molecular formula is C6H5ClFNO, 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. Application In Synthesis of (4-Chloro-5-fluoropyridin-2-yl)methanol

To a solution of Intermediate 47 (200 mg) in CH2Cl2 (5 ml) was added manganese oxide (861 mg). The suspension was stirred overnight and filtered eluting with CH2Cl2. The filtrate was concentrated in vacuo to afford 130 mg (66%) of the title compound as a yellow oil. 1H-NMR (delta, ppm, CDCl3): 10.00 (s, 1 H), 8.64 (s, 1 H), 8.06 (d, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 113209-90-8.

Reference:
Patent; GLAXO GROUP LIMITED; EP2080761; (2009); 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.23612-36-4, name is 3-Bromo-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.032, as common compound, the synthetic route is as follows.category: pyridine-derivatives

N-BOC-3-bromo-5-azaindole[00146] Referring now to the Scheme 1 as shown in Fig. 1 , a solution of 3.5601g(18.06 mmol) of 3-bromo-5-azaindole (2) and 0.4651 g (3.8 mmol, 21 mol%) of dimethylaminopyridine (DMAP) in 80 ml. of THF was placed in a 250 ml. three-neck round-bottom flask equipped with a magnetic stirrer, thermocouple, nitrogen bleed, and cooling ice bath. A total of 4.7769g (21.88 mmol, 1.2 eq.) of BOC2O was added to the flask at 17C, and the resulting mixture was stirred until starting 3-bromo-5-azaindole disappeared, as monitored by TLC (generally, overnight stirring at room temperature). The resulting yellow solution was concentrated on rotavap, washed with 100 ml. of saturated sodium bicarbonate, and extracted with dichloromethane (3×80 ml_). The organic phase was dried over Na2SO4 and concentrated on rotavap to afford 6.57g of orange solid. This crude material was purified on CombiFlash using hexane/ethyl acetate as eluent to give 5.25g (97% yield) of n-boc-3-bromo-5-azaindole (3) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23612-36-4, 3-Bromo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISIS INNOVATION LTD.; EBETINO, Frank, Hallock; MAZUR, Adam; LUNDY, Mark, Walden; RUSSELL, Robert, Graham, Goodwin; WO2010/33981; (2010); A2;,
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. 6515-09-9, name is 2,3,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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. Safety of 2,3,6-Trichloropyridine

General procedure: For the 5-subsititution was H, F or Cl, the procedure was as follows: A mixture of compound 7 (0.79 g, 5.25 mmol), 5-substituted-2,4-dichloropyrimidine (5 mmol) and DIPEA (1.05 mL,6 mmol) in i-PrOH was heated under reflux for 6 h.Water (100 mL)was added and the solid was filtered off, washed with water and driedto obtain compounds 10a-10c. For the 5-subsititution was methyl or methoxy, the procedure was as follows: To a mixture of compound 7 (1.26 g, 8.4 mmol) and5-substituted-2,4-dichloropyrimidine (8 mmol) was added NaH (60%, 0.38 g, 9.6 mmol) in DMF (6 mL) under ice bath. Then the mixture was stirred for 24 h at room temperature.Water was added dropwise to stop the reaction. The reaction mixture was extracted withdichloromethane (20 mL x 3), and the combined organic layer waswashed with brine (15mL x 2), dried over anhydrous Na2SO4 and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography to obtain compound 10d and 10e. 4.1.5.1. 2-((3,6-Dichloropyridin-2-yl)amino)benzamide (10a).Yield 80%. MP: 222-223 C.1H NMR (400 MHz, DMSO-d6) delta 12.27 (s,1H), 8.88 (d, J = 4.4 Hz, 1H), 8.55 (d, J = 8.0 Hz, 1H), 8.46 (s, 1H), 7.82(dd, J = 7.6, 0.8 Hz, 1H), 7.62-7.58 (m, 1H), 7.24-7.21 (m, 1H), 2.84(d, J = 4.8 Hz, 3H). 13C NMR (100 MHz, DMSO-d6) delta 168.70, 156.63,156.12, 155.25, 138.33, 131.84, 128.11, 123.06, 120.92, 120.77, 114.93,26.36.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75279-39-9 , The common heterocyclic compound, 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide, molecular formula is C7H9N3O, 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 a solution of 9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-6-phenoxy-9H-Purine (500 mg, 1.181 mmol) and 3-fluoropyridin-4-amine (529 mg, 4.72 mmol) in DMF (5 mL) was added a 60% dispersion of sodium hydride (236 mg, 5.90 mmol) in mineral oil and the mixture was stirred for 3 h. LCMS indicated completion of reaction. The reaction mixture was quenched carefully with water (25 mL) and allowed to stand for two hours. The resulting brown precipitate was filtered and washed with water followed by petroleum ether and dried to afford N-(3-fluoropyridin-4-yl)-9-(4-methoxybenzyl)-2-(6-methylpyridin-2-yl)-9H-purin-6-amine (400 mg, 0.634 mmol, 53.7 % yield) as a brown solid

The synthetic route of 75279-39-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Harikrishnan, Lalgudi S.; Warrier, Jayakumar; Tebben, Andrew J.; Tonukunuru, Gopikishan; Madduri, Sudhakara R.; Baligar, Vishweshwaraiah; Mannoori, Raju; Seshadri, Balaji; Rahaman, Hasibur; Arunachalam; Dikundwar, Amol G.; Fink, Brian E.; Fargnoli, Joseph; Fereshteh, Mark; Fan, Yi; Lippy, Jonathan; Ho, Ching-Ping; Wautlet, Barri; Sheriff, Steven; Ruzanov, Max; Borzilleri, Robert M.; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1026 – 1034;,
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. 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid

EXAMPLE 56 STR64 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)](320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1 NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0 Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0 Hz and 2.0 Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0 Hz and 1.0 Hz) Analysis Calcd. for C21 H23 N3 O: C 75.65, H 6.95, N 12.60. Found: C 75.75, H 7.01, N 12.66.

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, 80537-07-1, 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid.

Reference:
Patent; Fujisawa Pharmaceutical Company, Ltd.; US4925849; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem