Day: April 8, 2022

Reference of 105166-53-8 , The common heterocyclic compound, 105166-53-8, name is [2,2′-Bipyridin]-3-amine, molecular formula is C10H9N3, 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: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.(Z)-3-(2-(2,2?-bipyridin-3-yl)hydrazono)indolin-2-one (3), yellow solid (328 mg, 52%): 1H-NMR (600 MHz,DMSO): delta15.70 (s, 1H), 10.89 (s, 1H), 8.80 (d, J = 4.0 Hz, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.45 (dd, J = 8.4,1.3 Hz, 1H), 8.37 (dd, J = 4.3, 1.4 Hz, 1H), 8.04-7.98 (m, 1H), 7.62 (d, J = 7.4 Hz, 1H), 7.54-7.46 (m, 1H),7.25 (dd, J = 7.6, 6.7 Hz, 1H), 7.04 (t, J = 7.2 Hz, 1H), 6.92 (d, J = 7.7 Hz, 1H). 13C-NMR (151 MHz,DMSO) delta161.83, 156.74, 147.04, 142.28, 140.39, 139.61, 137.59, 137.13, 130.36, 128.95, 125.16, 123.13,121.90, 121.74, 121.61, 121.27, 119.08, 110.29. Elem. anal. calcd. for C18H13N5O, C 68.56, H 4.16, N 22.21.Found: C 68.48, H 4.09, N 21.88. IR (ATR) nu/cm-1: 3180, 3047, 1693, 1464, 1164, 798. m.p: 238-240 C.

The synthetic route of 105166-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
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 1052714-48-3, name is 6-Bromo-3-fluoropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Bromo-3-fluoropicolinic acid

6-Bromo-3-fluoro-2-methylpyridine (5 g, 26.3 mmol) was dissolved in 100 ml of water and potassium permanganate (12.5 g, 78.9 mmol) was added. The reaction mixture was heated to reflux for 12 h. Solid constituents were removed by filtration. The filter cake was washed three times with 100 ml of water. The collected wash solutions were concentrated and the crude product was obtained as white solid, which was further reacted directly. The crude product (6 g) was dissolved in 20 ml of dimethylformamide and, after adding sodium ethanethiolate (6.6 g, 78.9 mmol), the mixture was stirred for 12 h at room temperature. The reaction mixture was filtered and the organic phase was concentrated. The residue was purified by chromatography (mobile phase: water/acetonitrile) and the product was obtained in the form of a yellow solid. log P (neutral): 1.79; MH+: 262; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 7.85-7.39 (m, 2H), 3.34-2.92 (m, 2H), 1.39-1.15 (m, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1052714-48-3.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHSAFT; FISCHER, RUEDIGER; WILCKE, DAVID; KAUSCH-BUSIES, NINA; HAGER, DOMINIK; ILG, KERSTIN; HOFFMEISTER, LAURA; WILLOT, MATTHIEU; PORTZ, DANIELA; GOERGENS, ULRICH; TURBERG, ANDREAS; (161 pag.)US2018/271099; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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