Category: pyridine-derivatives

Synthetic Route of 89364-04-5, 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. 89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, 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.

Under a nitrogen stream3-bromo-4-nitropyridine 3.4g (16.9 mmol),5spiro [benzo [c] fluorene-7,9′-fluorene] -5-ylboronic acid, 8.3g (20.2 mmol) 1.0 g (5 mol%) of Pd (PPh3) 4, and potassium carbonate, 7.0 g (50.6 mmol)80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 C for 3 hours.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO4.The solvent of the organic layer was removed, and the residue was purified by column chromatography to give the desired compound B1 (5.9 g, 12.1 mmol, yield 72%).

According to the analysis of related databases, 89364-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Doosan Co., Ltd; Kim Hong-seok; Ra Jong-gyu; (52 pag.)KR2019/2183; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90395-45-2, 1-(4-(Pyridin-3-yl)phenyl)ethanone, 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, HPLC of Formula: C13H11NO, blongs to pyridine-derivatives compound. HPLC of Formula: C13H11NO

1-(4-pyridin-3-ylphenyl)-ethanone(1-(4-Pyridin-3-yl-phenyl)-ethanone) (75g, 380.26mmole),3-bromobenzaldehyde(3-bromo-benzaldehyde) (67g, 362.16mmole),Add 1340 ml of ethanol and stir in the reaction flask.Finally, sodium tert-butoxide (52.7 g, 543.23 mmole) was added and stirred at room temperature.After the reaction has been completed, add 200 ml of deionized water and stir to filter.After filtering the solid with deionized water and methanol,The solid was then filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes.The solid was dried twice to obtain 78 g of pale yellow solid 3-(3-bromophenyl)-1-(4-pyridin-3-ylphenyl)-acetone(3-(3-bromo-phenyl)-1-(4-pyridin-3-ylphenyl)propanone),The yield was 88.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90395-45-2, 1-(4-(Pyridin-3-yl)phenyl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Yulei Optoelectric Technology Co., Ltd.; Huang Helong; Guo Huangming; Zhao Dengzhi; Lin Qizhen; Zhang Minzhong; (29 pag.)CN109988159; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 121643-44-5, 2-Methoxy-3-(trifluoromethyl)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, 121643-44-5, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methoxy-3-(trifluoromethyl)pyridine

Intermediate 1 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 113.0 mmol) and 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18 h under argon. The TFA was removed in vacuo (50 mbar, 45 C.) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL). The filtrate was concentrated in vacuo, diluted with heptane/tert-butyl methyl ether (5/1, 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane/EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHCO3 (20 g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5 g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1H) 8.4 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 23056-47-5, 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. 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine, molecular formula is C6H5BrN2O2, 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.

Intermediate 6.1 : 2-bromo-5-nitro-pyridine-4-carboxylic acid To a solution of 2-bromo-4-methyl-5-nitropyridine (10 g, 46.5 mmol) in H2S04 (100 mL) was added Cr03 (15.5 g, 153 mmol) in portions at 0C. The reaction solution was stirred at 0C for 1 h and then warmed to ambient for 16 h. Then the solution was poured into a mixture of ice and water (300 mL), stirred at room temperature for 1 h, filtered to get a white solid, this target compound was used for the next step without any further purification.

According to the analysis of related databases, 23056-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEO PHARMA A/S; SOERENSEN, Morten Dahl; LARSEN, Jens Christian Hoejland; NOERREMARK, Bjarne; LIANG, Xifu; HUANG, Guoxiang; CHEN, Jinzhong; WO2013/82756; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188425-85-6, 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. 188425-85-6, name is 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide, molecular formula is C18H12Cl2N2O, 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.

Compound 2-chloro-N-(4′-chloro-5-hydroxybiphenyl-2-yl)nicotinamide, which is the main metabolite of boscalid, was prepared following the synthetic scheme depicted in Fig. 1. Briefly, phenyliodine(III) bis(trifluoroacetate) (PIFA, 451 mg, 1.049 mmol, 1.2 equiv) was added to a solution of boscalid (300 mg, 0.875 mmol) and trifluoroacetic acid (673 muL, 7.4 mmol, 10 equiv) in CHCl3 (11.5 mL). After stirring for 3 h at room temperature, the reaction mixture was cooled in an ice bath and then quenched by the addition of 5% NaHCO3 (30 mL). The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and dried over anhydrous MgSO4. The brownish residue left after evaporation of the solvent was purified by column chromatography, using CHCl3/CH3OH 99:1 as eluent, to afford metabolite M510F01. IR vmax/cm-1 (NaCl) 3377, 3230, 3028, 1652, 1580, 1394, 1088, 1012, 749; 1H NMR (300 MHz, CDCl3) delta 8.42 (1H, dd, J = 4.8, 1.8 Hz, H-6 Py), 8.03 (1H, dd, J = 7.8, 1.8 Hz, H-4 Py), 7.99 (1H, br s, NH), 7.82 (1H, d, J = 8.7 Hz, H-3 PhPh), 7.38-7.23 (5H, m, H-2’/H-6′, H-3’/H-5′ and H-5 Py), 6.81 (1H, dd, J = 8.7, 3 Hz, H-4 PhPh), 6.72 (1H, d, J = 3 Hz, H-6 PhPh); 13C NMR (75 MHz, CDCl3) delta 163.44 (CON), 154.17 (C-5 PhPh), 151.24 (C-6 Py), 146.85 (C-2Py), 139.82 (C-4 Py), 136.22 (C-3 Py), 135.73 (C-10), 134.27 (C-4’PhPh), 130.89 (C-2 PhPh), 130.41 (C-3’/C-5′ PhPh), 129.02 (C-2’/C-6′ PhPh), 126.13 (C-1 PhPh), 125.69 (C-5 Py), 122.88 (C-2 PhPh), 117.16 (C-4 PhPh), 115.71 (C-6 PhPh); HRMS (TOF MS), calculated for C18H1135Cl2N2O2 [M-H]+ 357.0198, found 357.0219.

According to the analysis of related databases, 188425-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Esteve-Turrillas, Francesc A.; Mercader, Josep V.; Agullo, Consuelo; Abad-Somovilla, Antonio; Abad-Fuentes, Antonio; Food Chemistry; vol. 267; (2018); p. 2 – 9;,
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 57963-08-3, name is 5,6-Dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H10N2

A pressure tube was charged with ethyl 4,6-dichloropyridazine-3-carboxylate (300 mg, 1.36 mmol), 5,6-dimethylpyridin-2-amine (249 mg, 2.04 mmol) in acetonitrile (8 mL) and the mixture was heated in an oil bath at 140 C. for 18 h. After cooling to room temperature, the mixture was concentrated in vacuo, adsorbed on silica gel and then purified by chromatography (silica, 50 mum, 80 g column from Analogix, 0% to 10% acetone in dichloromethane, 20 min) to afford ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate (150 mg, 36%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 10.20 (s, 1H) 8.86 (s, 1H) 7.57 (d, J=8.08 Hz, 1H) 6.97 (d, J=8.08 Hz, 1H) 4.40 (q, J=7.24 Hz, 2H) 2.42 (s, 3H) 2.23 (s, 3H) 1.35 (t, J=7.20 Hz, 3H); LCMS (EI/CI) m/z: 307 [M+H].

With the rapid development of chemical substances, we look forward to future research findings about 57963-08-3.

Reference:
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 23056-47-5, 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 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq) and NH4C1 (240 g, 4.49 mol, 4.87 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 50C. To this mixture was added Fe (120 g, 2.15 mol, 2.33 eq) and HC1 (10.2 g, 279 mmol, 0.30 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 Lx 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6- bromo-4-methylpyridin-3-amine (XV) as brown solid (167.9 g, 898 mmol, 97.4% yield) which was used for the next step without any purification. ?H NMR (CDC13, 400 MHz) ppm 2.15 (s, 3H), 3.44 (br s, 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

According to the analysis of related databases, 23056-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (240 pag.)WO2017/23975; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13296-04-3, 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 13296-04-3 as follows.

EXAMPLE 11 N-[4-(4-Pyridinyl)phenyl]butanamide–To a mixture containing 19.6 g. of n-butanoic acid anhydride in 150 ml. of chloroform was added with stirring 6.81 g. of 4-(4-pyridinyl)benzeneamine and the resulting mixture was stirred at room temperature for 17 hours and then refluxed with stirring for 90 minutes. The reaction mixture while warm was filtered through diatomaceous earth and the filtrate was concentrated on a steam bath to remove the solvent. The residue was diluted with water, the aqueous mixture made alkaline with ammonium hydroxide and the resulting mixture was stirred, concentrated further to remove small amount of remaining chloroform and the resulting solid was collected. The solid was recrystallized from 150 ml. of ethanol plus water and dried in vacuo at 90 C. for 20 hours to yield 8.2 g. of N-[4-(4-pyridinyl)phenyl]butanamide, m.p. 174-175 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13296-04-3, its application will become more common.

Reference:
Patent; Sterling Drug Inc.; US4317827; (1982); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 887115-56-2, 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 887115-56-2 as follows.

A mixture of 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (3.04 g, 14.0 mmol), bis(pinacolato)diboron (4.37 g, 17.0 mmol), PdCl2(dppf) (0.992 g, 1 mmol), and potassium acetate (3.52 g, 36 mmol) in dioxane was heated at 100 C. for 1 hour. Reaction mixture was portioned between ethyl acetate and saturated sodium bicarbonate solution, organic layer dried (MgSO4), filtered, concentrated and purified by CombiFlash (ethyl acetate/hexanes) to give desired product. LCMS-ESI+: calc’d for C13H19BN3O2: 260.2 (M+H)+; found: 260.2 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,887115-56-2, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Cai, Zhenhong R.; Guo, Hongyan; Ji, Mingzhe; Jin, Haolun; Lee, Amy; McFadden, Ryan; Mitchell, Michael L.; Munoz, Manuel; Pyun, Hyung-Jung; Xu, Lianhong; Yang, Hong; (272 pag.)US2018/118734; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1206775-52-1, 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.1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.

5-Bromo-6-methoxypyridine-2-carboxaldehyde (15 g, 69.3 mmol, 1 eq.) Was dissolved in 300 ml of dichloromethane, and the temperature was lowered to -78 C. Under nitrogen protection, diethylaminosulfur trifluoride (44.7 g, 277.2 mmol, 4 eq.) Was added dropwise. After completion of the dropwise addition, the reaction was carried out at 18 C for 18 hours.After the reaction was completed, the reaction solution was dropped into ice water and made alkaline with a saturated sodium bicarbonate solution. Extraction with dichloromethane, concentration of the organic phase and column chromatography gave 15 g of 3-bromo-6- (difluoromethyl) -2-methoxypyridine as a white solid with a yield of 91%.

Statistics shows that 1206775-52-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-6-methoxypicolinaldehyde.

Reference:
Patent; Ali Biological New Materials (Changzhou) Co., Ltd.; Shi Jianyun; Xu Yibo; Dai Hongsheng; Xu Xiangcheng; Liu Chao; (10 pag.)CN110724091; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem