Pyridine-derivatives

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.166526-03-0, name is 4,6-Dichloronicotinonitrile, molecular formula is C6H2Cl2N2, molecular weight is 173, as common compound, the synthetic route is as follows.Recommanded Product: 4,6-Dichloronicotinonitrile

4-Chloro-6-(l,3-dimethylpyrazol-4-ylamino) pyridine-3-carbonitrile was prepared as follows:4,6-Dichloropyridine-3-carbonitrile (9.60 g, 55.49 mmol), N-(l,3-dimethylpyrazol- 4-yl)acetamide (8.5 g, 55.49 mmol, see Example 2.02), palladium(II) acetate (0.374 g, 1.66 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.926 g, 3.33 mmol) and cesium carbonate (27.1 g, 83.23 mmol) were weighed out in a flask. Dioxane (110 mL) was added and argon was bubbled through the reaction mixture for 5 minutes at room temperature. The resulting suspension was stirred at 90 0C for 2 hours. The reaction mixture was allowed to cool to room temperature with stirring, water (275 mL) was added followed by the portionwise addition of lithium hydroxide hydrate (6.99 g, 166.47 mmol). The solution was left to stir at room temperature for 30 minutes. The resulting precipitate was collected by filtration, washed with water and dried. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in EtOAc/DCM (1 :1). The solvent was evaporated to dryness. The residue was triturated in Et2O, and the resulting precipitate was collected by filtration, washed with Et2O and dried to a constant weight to afford 4-chloro-6-(l,3-dimethylpyrazol-4-ylamino)pyridine-3-carbonitrile (6 g, 43.7 %) as a pale yellow solid. 1H NMR spectrum (500 MHz, CDCl3): delta 2.15 (s, 3H), 2.88 (s, 3H), 6.43 (s, IH), 6.45 (s, IH), 7.44 (s, IH), 8.36 (s, IH); Mass spectrum: m/z (ESI+) (M+H)+ = 248.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,166526-03-0, 4,6-Dichloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/153589; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 183208-35-7, 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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

A solution of 5-bromo- lH-pyrrolo[2,3-b]pyridine 8 (196 g, 994 mmol) in anhydrous tetrahydrofuran (2 L) was cooled to 0 C and treated with sodium hydride (60% in mineral oil, 49.3 g 1233 mmol) over 30 minutes. After two hours, benzenesulfonyl chloride 9 (153 mL, 1 193 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The reaction was quenched with brine (1 L). The layers were separated and the aqueous phase was extracted with ethyl acetate (2 x 500 mL). The organic layers were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure. The product was triturated with methyl tert-butyl ether to give compound 10 as a tan solid (319 g, 95%). The data from the lH NMR spectrum were consistent with the structure of the compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Reference:
Patent; PLEXXIKON INC.; WU, Guoxian; CHAN, Katrina; EWING, Todd; IBRAHIM, Prabha, N.; LIN, Jack; NESPI, Marika; SPEVAK, Wayne; ZHANG, Ying; WO2014/100620; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1201924-32-4 ,Some common heterocyclic compound, 1201924-32-4, molecular formula is C7H6ClNO2, 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.

6-Chloro-3-methylpyridine-2-carboxylic acid (595 mg, 3.47 mmol), aminomethylcyclopropane (356 muL, 4.16 mmol), EDC.HCl (1.46 g, 7.63 mmol), HOBN (1.54 g, 8.67 mmol) and NEM (1.10 mL, 8.67 mmol) were dissolved in DCM (30 mL) and stirred for 16 h. The reaction mixture was washed with sat aq NaHCO3 (30 mL), 1M aq HCl (30 mL), brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (215 mg, 28%) as a yellow solid. LCMS (ES+): 225.5 [MH]+.

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. 1201924-32-4, 6-Chloro-3-methylpicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Proximagen Limited; Savory, Edward Daniel; Stewart, Allson; Cartey, Allison; Brown, Giles; Simpson, Iain; Oliver, Kathryn; Patient, Lee; Higginbottom, Michael; Cole, Andrew Graham; US2013/289020; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 624-28-2, Adding some certain compound to certain chemical reactions, such as: 624-28-2, name is 2,5-Dibromopyridine,molecular formula is C5H3Br2N, 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 624-28-2.

SYNTHESIS OF INTERMEDIATE KETONE B2-(5-Bromopyridin-2-yl)- 1-(2,4-difluorophenyl)-2,2-difluoroethanone (B) To a suspension of copper powder (2.68 grams (g), 42.2 millimoles (mmol)) in dimethyl sulfoxide(DMSO; 35 milliliters (mL)) was added ethyl 2-bromo-2,2-difluoroacetate (2.70 mL, 21.10mmol), and the mixture was stirred for 1 hour (h) at room temperature (RT). 2,5-Dibromopyridine(2.50 g, 10.55 mmol) was then added, and stirring was continued for 15 h at RT. The reactionmixture was quenched with aqueous (aq) ammonium chloride (NH4C1) and extracted withdichloromethane (CH2C12 3 x 25 mL). The combined organic layers were washed with water (H20), washed with brine, dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford the crude product mixture. Purification by column chromatography (eluting with ethyl acetate (EtOAc)/hexane) afforded the ethyl ester intermediate (2.40 g, 8.57mmol, 81%) as a pale yellow oil. ?H NMR (500 MHz, CDC13): oe 8.71 (s, 1H), 8.00 (d, J 9.0 Hz,1H), 7.64 (d, J= 9.0 Hz, 1H), 4.42-4.35 (m, 2H), 1.39-1.3 1 (m, 3H).

According to the analysis of related databases, 624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; GUSTAFSON, Gary, D.; HOEKSTRA, William, J.; LOSO, Michael, R.; YATES, Christopher, M.; WO2014/43376; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13603-44-6, 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 13603-44-6, name is 2,6-Dimethylpyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

Bromine (72.8 mL, 1.4 mol) was added via addition funnel over 60 min to a mechanically stirred cold (ice-water bath) solution of 2,6-dimethylpyridin-4- ol (87 g, 706 mmol) and 4-methylmorpholine (156 mL, 1.4 mol) in dichloromethane (1 L) and methanol (100 mL) and then stirred for 2 h at rt. Additional bromine (-15 mL) was added based on monitoring by LCMS. The product was filtered, washed with ether, and dried under vacuum to give 3,5-dibromo-2,6-dimethylpyridin-4-ol 176.8 g (88%).

According to the analysis of related databases, 13603-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; EASTMAN, Kyle J.; KADOW, John F.; PARCELLA, Kyle E.; NAIDU, B. Narasimhulu; WANG, Tao; YIN, Zhiwei; ZHANG, Zhongxing; (121 pag.)WO2017/25917; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 885588-03-4, Adding some certain compound to certain chemical reactions, such as: 885588-03-4, name is 3-((2-Fluoro-4-iodophenyl)amino)isonicotinic acid,molecular formula is C12H8FIN2O2, 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 885588-03-4.

2.7 N-[(3aS,4R,7aR)-2,2-dimethylhexahydro-1 ,3-benzodioxol-4-yl]-3-[(2-fluoro-4- odophenyl) amino]isoicotinamide (31); A suspension of 3-[(2-fluoro-4-iodophenyl) amino] isonicotinic acid (10.46 g, 29.2 mmol), (3aS,4fi,7afi)-2,2-dimethylhexahydro-1 ,3-benzodioxol-4-amine (21 ) (5.00 g, 29.2 mmol), 1 – hydroxybenzotriazole (4.41 g, 29.2 mmol) and EDCI (5.6 g, 29.2 mmol) in DMF (100 mL) was stirred at room temperature overnight. The reaction was quenched with water (150 mL) and extracted with ethyl acetate (150 mL). Emulsion was formed and collected, filtered and the filtrate was combined to the organic layer. The organic layer was washed with saturated NaHCO3 solution (150 mL) and water (2×150 mL), brine and dried over Na2SO4 and concentrated to give brown foam. The crude was purified by crystallization from IPA. The mother liquor was concentrated and purified by flash chromatography to afford the desired product (12 g. 80% yield). LC/MS [Method A: rt:7.35 min; m/z: 512 (M+1 )].

According to the analysis of related databases, 885588-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; GOUTOPOULOS, Andreas; YU, Henry; ASKEW, Benny, C.; LIU-BUJALSKI, Lesley; WO2010/17051; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1190319-59-5, 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.1190319-59-5, name is 1H-Pyrrolo[2,3-c]pyridine-4-carbonitrile, molecular formula is C8H5N3, molecular weight is 143.1454, as common compound, the synthetic route is as follows.

a) To a suspension of NaH 60% (19 mg, 0.47 mmol) in dry DMF (1 mL) at 0 5C was added dropwise a solution of 1 H-pyrrolo[2,3-c]pyridine-4-carbonitrile (67 mg, 0.45 mmol) in DMF (1 mL). After 10 min a solution of 2-(bromomethyl)-4- chloro-1 -((2,4-difluorobenzyl)oxy)benzene (162 mg, 0.47 mmol) in 1 mL of DMF was added dropwise. After 16 h at 0 5C water was added and extracted with EtAcO (x3). Combined organic extracts were washed with water, brine and dried over Na2S04. Column chromatography on silica gel eluting with DCM:MeOH (95:5) gave the desired compound as a slightly brown solid (159 mg, 87% yield).1 H NMR (400 MHz, CDCI3) ? 8.83 (s, 1 H), 8.55 (s, 1 H), 7.37 (d, J = 3.1 Hz, 1 H), 7.29 (dd, J = 8.8, 2.6 Hz, 1 H), 7.22 – 7.14 (m, 1 H), 6.99 (d, J = 2.6 Hz, 1 H), 6.94 (d, J = 8.8 Hz, 1 H), 6.90 – 6.82 (m, 2H), 6.70 (dd, J = 3.1 , 0.8 Hz, 1 H), 5.37 (s, 2H), 5.04 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 1190319-59-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 88912-26-9, 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 88912-26-9 as follows.

THF (25 ml_), 2-{4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2- fluorophenyl}acetohydrazide (700 mg, 1.98 mmol), 2,5-dichloro-4-pyridinecarboxylic acid (380 mg, 1.98 mmol), HATU (380 mg, 1.98 mmol) and DIPEA (0.700 ml_, 3.96 mmol) were combined and stirred at rt for 45 min. Burgess Reagent (2.36 g, 9.90 mmol) was added and the reaction stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The solvent was removed and the crude material purified via silica gel chromatography to give 340 mg of the title compound. 1H NMR (DMSO-d6) delta 8.74 (s, 1 H), 7.98 (s, 1 H), 7.77 (m, 1 H), 7.50 (m, 3 H), 7.46 (m, 1 H), 4.50 (s, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,88912-26-9, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 74420-15-8, 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 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A. 3-Bromo-1H-pyrrolo[2,3-b]pyridine and ammonia (0.5M in 1,4-dioxane) is heated to reflux. After 5 h the solution is concentrated. The residue is chromatographed on a silica gel plug to give 1H-pyrrolo[2,3-b]pyridin-3-ylamine.

According to the analysis of related databases, 74420-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6635-90-1, 2-Methoxy-4-methyl-5-nitropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

1. The mixture of 2-methoxy-4-methyl-5-nitropyridine (1.68g, 10.0 mmol) and 1,1- dimethoxy-N,N-dimethylmethanamine (14 Ml, 103 mmol) in 10 mL of DMF was heated at 130C overnight, cooled to RT, diluted with EtOAc, washed with water and brine, dried (MgS04), and concentrated. The residue was dissolved in 70 mL of EtOH. To this solution was added 1.06 g of 10% Pd/C. The mixture was stirred under 1 atm of hydrogen atmosphere over 4 days, filtered through a pad of Celite, and washed with EtOH. The filtrate was concentrated to give crude 5-methoxy-lH-pyrrolo[2,3-c]pyridine (quant). H NMR (399 MHz, DMSO-d6) delta ppm 11.26 (1 H, br. s.), 8.33 (1 H, s), 7.53 (1 H, d, 7=2.7 Hz), 6.73 – 6.88 (1 H, m), 6.32 (1 H, d, 7=3.1 Hz), 3.30 (3 H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6635-90-1, 2-Methoxy-4-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; SRI INTERNATIONAL; JONG, Ling; CHANG, Chih-Tsung; PARK, Jaehyeon; (71 pag.)WO2016/114816; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem