Pyridine-derivatives

Synthetic Route of 1446507-38-5, 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. 1446507-38-5, name is 6-(6-(Trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

POCl3 (175.0 mL) is charged into the reaction vessel at 20-35 C., and 6-(6-trifluoromethyl-pyridin-2-yl)-1H-1,3,5-triazine-2,4-dione (35.0 g, 0.1355 mol) was added in portions at below 50 C. The reaction mixture was de-gassed 5-20 minutes by purging with N2 gas. Phosphorous pentachloride (112.86 g, 0.542 mol) was added while stirring at below 50 C., the resulting slurry was heated to reflux (105-110 C.) and maintained for 3-4 h. The reaction mixture was cooled to 50-55 C., concentrated at below 55 C. then cooled to 20-30 C. The reaction mixture was rinsed with ethyl acetate and the ethyl acetate layer was slowly added to cold water (temperature 5 C.) while stirring and maintaining the temperature below 10 C. The mixture was stirred 3-5 minutes at a temperature between 10 to 20 C. and the ethyl acetate layer was collected. The reaction mixture was rinsed with sodium bicarbonate solution and dried over anhydrous sodium sulphate. The material was dried 2-3 h under vacuum at below 45 C. to provide 2, 4-dichloro-6-(6-trifluoromethyl-pyridin-2-yl)-1, 3, 5-triazine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1446507-38-5, 6-(6-(Trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; Agios Pharmaceuticals, Inc.; Agresta, Samuel V.; (34 pag.)US2018/311249; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 603305-89-1, 7-Bromothieno[3,2-b]pyridine, 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, 603305-89-1, blongs to pyridine-derivatives compound. Recommanded Product: 603305-89-1

General procedure: A dry Schlenk tube was charged under Ar with dry toluene (3 mL), the fluoro or methoxyanilines (1.1 equiv.), Pd(OAc)2 (6 mol%), BINAP (8 mol%), Cs2CO3 (2 equiv.) and compound 1. The mixture was heated with stirring under Ar at 100 C for 2 h. After cooling water (5 mL) and ethyl acetate (5 mL) were added. The phases were separated and the aqueous phase was extracted with more ethyl acetate (2 × 5 mL). The organic phase was dried (MgSO4) and filtered. Removal of the solvent gave a solid which was submitted to a dry flash in silica using ether or AcOEt and a solid was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,603305-89-1, its application will become more common.

Reference:
Article; Queiroz, Maria-Joao R.P.; Peixoto, Daniela; Calhelha, Ricardo C.; Soares, Pedro; Dos Santos, Tiago; Lima, Raquel T.; Campos, Joana F.; Abreu, Rui M.V.; Ferreira, Isabel C.F.R.; Vasconcelos, M. Helena; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 855 – 862;,
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 4021-11-8, name is 2-Methylisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 4021-11-8

A suspension of 2-methyl-pyridine-4-carboxylic acid (1.0 g, 7.29 mmol) in methanol (50 ml_) and H2SO4 (0.5 ml_) is heated to 700C. The solid material dissolves and stirring is continued at 700C for 18 h. The mixture is cooled to rt, filtered, and the filtrate is evaporated. The remaining solid is washed with diethyl ether and dried to give methyl 2-methyl-pyridine-4-carboxylate; LC-MS: tR = 0.39 min, [IVM]+ = 152.05. This material is dissolved in 7 N NH3 in methanol (25 ml_) and the mixture is stirred in a sealed vial for 20 h at 60C before it is filtered. The filtrate is evaporated to give crude 2-methyl-isonicotinamide (2.12 g) as a brownish solid. To a solution of this material in DCM (25 ml_), pyridine (5.24 g, 54.0 mmol) is added. The mixture is cooled to 00C before trifluoroacetic anhydride (8.10 g, 38.6 mmol) is added portionwise. Stirring is continued at 00C for 2 h before the reaction is quenched with water. The mixture is diluted with DCM and the org. phase is separated and washed with 5% aq. citric acid solution followed by sat. aq. NaHCO3 solution. The washings are extracted back twice with DCM. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates with heptane:EA 4:1 to give 2-methyl-isonicotinonitrile (330 mg); LC-MS: tR = 0.55 min, [M+1]+ = 119.13.

With the rapid development of chemical substances, we look forward to future research findings about 4021-11-8.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/24905; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 911434-05-4, Adding some certain compound to certain chemical reactions, such as: 911434-05-4, name is 5-Bromo-2-methyl-3-nitropyridine,molecular formula is C6H5BrN2O2, 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 911434-05-4.

0208] Step 1. 5-Bromo-2-methyl-pyridin-3-ylamine. To a stirred mixture of iron filings (5 g, 89.29 mmol, 3.88 equiv) and ammonium chloride (1 g, 18.70 mmol, 0.81 equiv) in ethanol (66 mL) and water (33 mL) was added a solution of 5-bromo-2-methyl-3- nitropyridine (5 g, 23.04 mmol, 1.00 equiv) in ethanol (50 mL) dropwise at 90 C. The reaction mixture was stirred for 10 min at 90 C and then cooled to rt. The solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:2) to yield 1.6 g (37%) of the title compound as a yellow solid. LC/MS (Method I, ESI): RT= 0.81 min, m/z = 187.0; 189.0 [M+H

According to the analysis of related databases, 911434-05-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; BUCKMELTER, Alexandre, J.; CLODFELTER, Karl, H.; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; REYNOLDS, Dominic, J.; SMITH, Chase, C.; WANG, Zhongguo; ZAK, Mark; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/130943; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130658-65-0, 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. 130658-65-0, name is 1-(Pyridin-4-yl)piperidin-4-ol, molecular formula is C10H14N2O, 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.

EXAMPLE 31 Azodicarbonyldipiperidine (20.03 g), tributylphosphine (16.06 g) and 1-(4-pyridyl)-4-piperidin-1-ol (9.43 g) were added to a stirred solution of N-t-butyloxycarbonyl-4-aminophenol (11.08 g) in dry THF (300 ml), cooled under a blanket of nitrogen to 10 C. A thick precipitate formed and the mixture was stirred at ambient temperature for 20 hours during which time the mixture slowly thinned. The precipitated tributylphosphine oxide was removed by filtration and the residue concentrated in vacuo. The residue was purified by flash chromatography on silica gel using ethyl acetate followed by dichloromethane containing an increasing amount of methanol (up to 5% methanol) as eluent to give a solid (7.38 g). mp 192-195 C. A solution of this solid (4.22 g) in dichloromethane (400 ml) was treated with a saturated solution of hydrogen chloride in ether (50 ml) and the mixture was stirred for 64 hours. The mixture concentrated in vacuo and the residue crystallized from methanol/ether to give 1-(4-pyridyl)-4-(4-aminophenyloxy)piperidine hydrochloride (2.85 g), mp. 289-291 C. NMR: 1.73 (m,2H), 2.06 (m,2H), 3.64 (m,2H), 3.94(m,2H), 4.76 (m,1H), 7.12(d,2H), 7.24(d,2H), 7.34(d,2H), 8.23(d,2H), 10.32 (broad, 2H); MS: m/z 270 (MH)+. This solid (1.5 g) was dissolved in water (10 ml) and 2M sodium hydroxide added until precipitation was complete.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 130658-65-0, 1-(Pyridin-4-yl)piperidin-4-ol.

Reference:
Patent; Zeneca Limited; US6313127; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1235342-53-6, 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. 1235342-53-6, name is 3-(Bromomethyl)-5-methylpyridine hydrobromide. A new synthetic method of this compound is introduced below.

An inert atmosphere N2 was passed through a 1 L three-necked round bottom flask and held.3-Bromomethyl-5-methylpyridine hydrobromide (Compound A, 20 g, 74.92 mmol) was added.Dichloromethane (200ml) and water (40g),Then, sodium hydrogencarbonate (27.1 g, 322.58 mmol) was added dropwise with stirring at 0 C.Aqueous solution (40ml)And m-CPBA (37.1g, 214.99mmol)A solution of dichloromethane (200 ml).Stir at room temperature for 2 hours.The resulting solution was extracted with 5 x 200 ml of dichloromethane.Combine the organic layers,Dry with anhydrous sodium sulfate,Concentrate in vacuo.The residue was applied to a silica gel column eluting with dichloromethane/methanol.Get 7.5g (50%)Compound B3-bromomethane-5-methylpyridine-N-oxide pale yellow solid,The test results are shown in Figure 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1235342-53-6, 3-(Bromomethyl)-5-methylpyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Aoyi Baoling Pharmaceutical Co., Ltd.; Fang Yuan; Jin Yukun; Gong Wen; Li Fugao; Sun Xiaoyan; Ling Jue; Yu Yingmin; (15 pag.)CN109678841; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 117519-09-2, 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. 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H4ClF3N2, 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.

PREPARATION 173; 4-Bromo-2-chloro-6-trifluoromethyl-pyridin-3-ylamine; 6-Trifluoromethyl-pyridin-3-ylamine (150 g, 925 mmol) was suspended in 500 ml acetonitrile. Added to the solution was N-Chlorosuccinimide (124 g, 925 mmol) and the mixture heated at 80 C. for 2 h after which N-bromosuccinimide (165 g, 925 mmol) was added and the mixture heated at 80 C. for a further 3 h. The rm was cooled to ambient temperature, concentrated in vacuo and triturated in 100 ml diethyl ether, removing the precipitate by filtration. The resulting filtrate was concentrated in vacuo and purified by column chromatography on silica, eluting with Hept:EtOAc, 4:1 to give the title compound as a dark red oil (220 g, 86%).1H NMR (CDCl3) 4.90 (bs, 2H), 7.67(s, 1H); LRMS (ES) m/z 275/277 [MH]+

According to the analysis of related databases, 117519-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; US2007/197478; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71469-93-7, Methyl 4-aminopyridine-2-carboxylate, 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, 71469-93-7, blongs to pyridine-derivatives compound. Formula: C7H8N2O2

To a solution of 2-(2-methoxyphenyl)acetic acid (218 mg, 1.31 mmol) in DMF (4 mL) was added HOAt (179 mg, 1.31 mmol), EDCI (328 mg, 1.71 mmol), DIPEA (574 muL, 3.29 mmol) and methyl 4-aminopyridine-2-carboxylate (200 mg, 1.31 mmol) and the mixture was stirred at room temperature for 6 hours 15 minutes. The resulting mixture was partitioned between H2O (30 mL) and DCM (30 mL) and the two phases separated. The aqueous was further extracted with DCM (30 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with EtOAc in heptane to afford the titled compound as a pale yellow gum.1H NMR (500 MHz, Chloroform-d) delta 8.58 (d, J = 5.5 Hz, 1H), 8.10 (s, 1H), 7.92 (dd, J = 5.5, 2.2 Hz, 1H), 7.84 (d, J = 2.1 Hz, 1H), 7.37- 7.32 (m, 1H), 7.29 (dd, J = 7.4, 1.5 Hz, 1H), 7.04- 6.97 (m, 2H), 3.98 (s, 3H), 3.97 (s, 3H), 3.75 (s, 2H).LC-MS (Method E): Rt 0.96 mins; MS m/z 301.1 = [M+H]+ (99% 215nm)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71469-93-7, its application will become more common.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; COLLINGWOOD, Stephen; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; ELLAM, Sarah; BUXTON, Craig; HABGOOD, Matthew; INGRAM, Peter; MA, Chun Yan; NAPIER, Spencer; SHAIKH, Abdul; SMITH, Matthew; STIMSON, Christopher; WALKER, Edward; (401 pag.)WO2019/145726; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 183208-35-7 ,Some common heterocyclic compound, 183208-35-7, molecular formula is C7H5BrN2, 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.

Step 1: (0558) To a solution containing compound 6 (2.0 g, 10.15 mmol) dissolved in N,N-dimethylformamide (78.93 mL, 1015.05 mmol) was added 1-iodopyrrolidine-2,5-dione (2.28 g, 10.15 mmol) and the solution was allowed to stir at room temperature for 2 hours. Upon completion, the reaction mixture was poured into a saturated aqueous sodium thiosulfate solution and extracted with ethyl acetate (3×150 mL). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and then evaporated to dryness to give 3.15 grams of compound 7 in about 95% purity.

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.; Lin, Jack; Pham, Phuongly; Buell, John; Dong, Ken; Ibrahim, Prabha; Spevak, Wayne; Tsang, Garson; Wu, Guoxian; Zhang, Ying; (183 pag.)US2016/326162; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 70201-43-3, 3-Bromoisonicotinaldehyde, 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: C6H4BrNO, blongs to pyridine-derivatives compound. Formula: C6H4BrNO

[0068] To a solution of 3-bromo-4-pyridinecarboxaldehyde 3 (3.0 g, 16.2 mmol) in absolute methanol (40 mL) was added NaBH4 (0.736 g 19.5 mmol) at 0C. The mixture was stirred at 0C for 2 hours under nitrogen. The solvent was then removed under vacuum. Water and ethyl acetate were added and the organic layer was washed with water, dried over Na2SO4 and evaporated under vacuum to afford the compound 4 (3.021 g, 100%) as a white powder. 1H NMR (CDCl3, 300 MHz, 298 K, delta ppm): 8.61 (s, 1 H), 8.51 (d, 1H, J = 4.8 Hz), 7.55 (d, 1H, J = 4.8 Hz), 4.76 (s, 2 H), 2.89 (s, 1H). 13C NMR (CDCl3, 75.5 MHz, 298 K, delta ppm): 151.14, 149.45, 148.54, 122.47, 119.90, 63.47. GC/MS (m/z): 188 IR (KBr, v, cm-1): 3152, 2894, 2829, 1593, 1447, 1401, 1333, 1223, 1170, 1070, 1024, 834, 705, 599

The synthetic route of 70201-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSA (Institut National des Sciences Appliquees) de Rouen; Centre National de la Recherche Scientifique (CNRS); Universite de Rouen; VFP Therapies; Marsais, Francis; Levacher, Vincent; Papamicael, Cyril; Bohn, Pierre; Peauger, Ludovic; Gembus, Vincent; Le Fur, Nicolas; Dumartin-Lepine, Marie-Laurence; EP2759536; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem