Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 178876-83-0, Methyl 6-amino-3-bromopicolinate, 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, Computed Properties of C7H7BrN2O2, blongs to pyridine-derivatives compound. Computed Properties of C7H7BrN2O2

Example 57D methyl 3-bromo-6-fluoropicolinate To a solution of nitrosonium terafluoroborate (17.8 g) in dichloromethane (100 mL) at 5 C. was added EXAMPLE 57C (26.1 g) in dichloromethane (250 mL) over 1 hour. The reaction mixture was stirred an additional 30 minutes at 5 C., and allowed to warm to room temperature overnight. The reaction mixture was quenched with pH 7 buffer (100 mL), and neutralized with solid potassium carbonate. The resulting mixture was extracted with ether (twice), and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel using 1-10% ethyl acetate in hexanes to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178876-83-0, Methyl 6-amino-3-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Formula: C6H8BrN3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

Step 3. 5-bromo-N3-isopropyl-N2-methylpyridine-2.3-diamine and 6-bromo-2,2,3-trimethyl-2.3-dihydro- 1H-imidazor4.5-blpyridine; 5-bromo-N2-methylpyridine-2,3-diamine (54.4 mg, 0.269 mmol) was dissolved in isopropyl acetate (1.5 ml) and acetone (23 mul, 0.31 mmol), trifluoroacetic acid (0.045 ml, 0.58 mmol), and sodium triacetoxyborohydride (64 mg, 0.30 mmol) were added. The reaction was stirred under nitrogen at room temperature for 4 hours, and then more acetone was added (0.040 ml) along with TFA (0.090 ml) and isopropyl acetate (0.5 ml). The reaction was then stirred overnight. This reaction was repeated on a larger scale using 5-bromo-N2-methylpyridine-2,3-diamine (288 mg, 1.43 mmol), 2,2,2-trifluoroacetic acid (0.30 ml, 3.9 mmol), acetone (0.13 ml, 1.8 mmol), and sodium triacetoxyborohydride (352 mg, 1.66 mmol). Then, both reactions were poured into water (25 ml), and solid sodium hydroxide was added to raise the pH to about 10. The layers were separated, and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum. To afford 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine and 6-bromo-2,2,3- trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine (399 mg, 97% combined yield). 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine: MS (ESI pos. ion) m/z: 244 (MH+, 79Br), 246 (MH+, 81Br). Calculated exact mass for C9H14BrN3 243 (79Br), 245 (81Br). 6-bromo-2,2,3-trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine: MS (ESI pos. ion) m/z: 242 (MH+, 79Br), 244 (MH+, 81Br). Calculated exact mass for C9H12BrN3 241 (79Br), 243 (81Br).

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

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1721-23-9, 3-Cyano-2-methylpyridine, 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: 1721-23-9, blongs to pyridine-derivatives compound. SDS of cas: 1721-23-9

1-Amino-3(2-methyl-3-pyridyl)2,5-naphthyridine To 5.9 of 3-cyano-2-methylpyridine dissolved in 30 ml. of dimethylformamide, gradually add 6.7 g. of potassium t-butoxide at about 5 C. Maintain the mixture at 5 C for 4-6 hours and quench the reaction in ice water. Collect the crystalline precipitate and recrystallize from toluene to yield 1-amino-3(2-methyl-3-pyridyl)-2,5-naphthyridine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1721-23-9, 3-Cyano-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US4017500; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 872355-72-1, Adding some certain compound to certain chemical reactions, such as: 872355-72-1, name is Ethyl 5-amino-3-methoxypicolinate,molecular formula is C9H12N2O3, 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 872355-72-1.

To a N,N-dimethylformamide (10 mL) solution of ethyl 3-methoxy-5-aminopyridine- 2- carboxylate (300 mg, 1.53 mmol) was added iodine (388 mg, 1.53 mmol)) and sodium metaperiodate (327 mg, 1.53 mmol). The reaction was then heated to 60 0C for 18 h. After cooling to room temperature, the reaction was poured into a solution of sodium metabisulfite. The solid thus separated was filtered, washed with water and dried under high vacuum (Yield: 350 mg).

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. 872355-72-1, Ethyl 5-amino-3-methoxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178421-21-1, Adding some certain compound to certain chemical reactions, such as: 178421-21-1, name is Ethyl 6-chloro-5-methylpicolinate,molecular formula is C9H10ClNO2, 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 178421-21-1.

Step 1: 2-Carboxamido-5-methyl-6-chloropyridine (IX). Dissolve 26 g of 2-ethoxycarbonyl-5-methyl-6-chloro-pyridine (crude oil containing about 60% of ester) in 130 ml of methanol.Add 200 ml of 32% aqueous ammonia and stir overnight at room temperature.The product is recovered by filtration and gives, after washing with water and drying under vacuum, 13 g of white crystals. m.p.=146 C.

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. 178421-21-1, Ethyl 6-chloro-5-methylpicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Maurel, Jean-Louis; Bonnaud, Bernard; Ribet, Jean-Paul; Vacher, Bernard; US2004/116705; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909187-64-0, 6-Benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3(2H)-one, 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, 909187-64-0, blongs to pyridine-derivatives compound. Product Details of 909187-64-0

A mixture of 6-benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-ol (2.00 g, 8.72 mmol) and palladium on carbon (0.200 g, 1.88 mmol, Aldrich) in MeOH (100 mL) was stirred under H2 atmosphere for 48 h. The mixture was filtered through Celite and the filter cake was washed with MeOH. The mixture was concentrated in vacuo. The filter cake was washed with water and the filtrate was concentrated in vacuo. Both fractions contained the title compound. MS (ESI, pos. ion) m/z: 140 (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,909187-64-0, its application will become more common.

Reference:
Patent; Amgen Inc.; US2006/199817; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7477-10-3 , The common heterocyclic compound, 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, molecular formula is C6H3ClN2O4, 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: A solution of compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid.4.2.4.5 5-Nitro-6-(4-pyrimidin-2-ylpiperazin-1-yl)nicotinic acid (6e) Procedure A was used with compound 5 (170 mg, 0.84 mmol) and 1-(2-pyrimidyl)piperazine (278 mg, 1.7 mmol) to afford product 6e as a yellow solid (106 mg, 38%). 1H NMR (300 MHz, CDCl3) delta: 8.83 (d, J = 2.1 Hz, 1H), 8.56 (d, J = 2.1 Hz, 1H), 8.41 (d, J = 8.4 Hz, 2H), 6.70 (t, J = 4.8 Hz, 1H), 3.90-3.86 (m, 4H), 3.66-3.62 (m, 4H). ESI-MS: m/z (329, MH-).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1227270-32-7, 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 1227270-32-7 as follows.

In a vial, 2-iodo-1H-pyrrolo[2,3-b] pyridine 18a (200 mg, 0.82 mmol, 1 eq.) was dissolved in 8 ml of acetonitrile. Then 0.4 ml of acetic acid followed by 182 mg of Eschenmoser’s salt (0.98 mmol, 1.2 eq.) were added. After sealing the vial, the reaction mixture is stirred for 20 h at room temperature. 15 ml of a 2M solution of potassium hydroxide is added slowly and then the organic phase was extracted with ethyl acetate (3×20 ml). The organic phases are combined and then dried over MgSO4, filtered through cotton and evaporated to dryness. Finally, the crude is triturated with pentane and then vacuum filtered to obtain compound 174 (190 mg, 77%) as a yellow solid. Rf=0.10 (methanol/dichloromethane=2/98) mp=142-144 C. IR (v, cm-1, neat) 2957, 2932, 2851, 2812, 2768, 1603, 1580, 1514, 1489, 1448, 1407, 1369, 1354, 1328, 1287, 1273, 1248, 1206, 1167, 1147, 1121, 1094, 1036, 1004, 978, 905, 842. 1H NMR (400 MHz, CDCl3, 20 C.) delta 13.08 (s1, 1H), 8.41 (dd, J=4.9, 1.4 Hz, 1H), 8.09 (dd, J=7.9, 1.4 Hz, 1H), 7.11 (dd, J=7.9, 4.8 Hz, 1H), 3.60 (s 2H), 2.33 (s, 6H). 13C NMR (101 MHz, CDCl3, 20 C.) delta 151.0 (Cq), 142.0 (CH), 127.4 (CH), 121.3 (Cq), 116.7 (Cq), 115.8 (CH), 82.9 (Cq) 56.1 (CH2), 45.4 (2×CH3). HRMS (+ESI) calculated for C10H12IN3 (M+H+): 302.0148, found: 302.0148.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227270-32-7, its application will become more common.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE D’ ORLEANS; UNIVERSITE FRANCOIS RABELAIS DE TOURS; CENTRE HOSPITALIER REGIONAL UNIVERSITAIRE DE TOURS; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE; ROUTIER, Sylvain; SUZENET, Franck; CHALON, Sylvie; BURON, Frederic; VERCOUILLIE, Johnny; MELKI, Ronald; BOIARYNA, Liliana; GUILLOTEAU, Denis; PIERI, Laura Ronald; (144 pag.)US2019/211011; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1072-98-6 ,Some common heterocyclic compound, 1072-98-6, molecular formula is C5H5ClN2, 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 2-amino-5-chloropyridine (2.0 g, 16 mmol) [Matrix Scientific, 021118] in acetone (39 mL) was treated with ethyl bromopyruvate (2.2 mL, 16 mmol) and heated at 60 C for 45 min. The reaction mixture was cooled to 20 C and the suspension was filtered. The solid that was collected was washed with a small amount of cold acetone and dried in vacuo. The solid was diluted with ethanol (12 mL) and water (19 mL), heated at 65 C, and treated with sodium bicarbonate (1.6 g, 19 mmol) portionwise. The reaction mixture was cooled to 20 C and the suspension was filtered. The solid that was collected was washed with water (4 x 80 mL) and dried in vacuo to give the desired product (2.6 g, 74%). LCMS for Ci QHI 0CIN2O2(M+H)+: m/z = 225.1.

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. 1072-98-6, 2-Amino-5-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; LI, Yun-Long; YUE, Eddy W.; SPARKS, Richard B.; WO2011/75643; (2011); 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.1211517-76-8, name is 3-Bromo-5-fluoro-4-methylpyridine, molecular formula is C6H5BrFN, molecular weight is 190.013, as common compound, the synthetic route is as follows.Formula: C6H5BrFN

Step D 3-fluoro-4-methyl-5-f4 A5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl) yridme3-bromo-5-fluoro-4-methylpyridine (9.25 mmol, 2.93 g) bis(pinacolato)diboron (11.10 mmol, 2.82 g) l, -bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.463 mmol, 0.335 g) and potassium acetate (18.50 mmol, 1.816 g) were combined in dioxane (37.0 mL) and heated to 80 C for 24 hours, under nitrogen. The reaction was allowed to cool to room temperature, EtOAc (400ml) added and the mixture filtered through CELITE and washed with 1 :1 saturated sodium bicarbonate solution / water (2 x 200ml) and brine (100ml). Organics were dried over sodium sulphate and solvent evaporated under reduced pressure to yield crude product as a brown oil. Purification by silica chromatography eluting with 25 to 50% EtOAc / heptane afforded 3-fluoro-4-methyl-5-(4J4,5,5-tetramethyl-l.3,2-dioxaborolan-2-yl)pyridine. 1H NMR (CDC13)5: 8.68 (s, IH), 8.39 (s, 1H), 2.48 (s, 3H), 1.38 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HOYT, Scott, B.; PARK, Min, K.; LONDON, Clare; XIONG, Yusheng; BENNETT, D., Jonathan; CAI, Jaiqiang; RATCLIFFE, Paul; COOKE, Andrew; CARSWELL, Emma; MACLEAN, John; SAXENA, Rohit; KULKARNI, Bheemashankar, A.; GUPTA, Archana; WO2012/12478; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem