Pyridine-derivatives

Electric Literature of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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.

Under nitrogen protection, to 6 mL of dioxane was added 5-bromo-3-methyl-lH- pyrazolo[3,4-c]pyridine from Example 102 (0.21 g, 1 mmol), 3-fluorophenylboronic acid (0.28 g, 2 mmol), PdCl2(dppf) (87 mg, 0.1 mmol) and 2 M Na2C03 (2 mmol, 1 mL). The suspension was heated under microwave radiation at 130 C for 1 hour. It was cooled to room temperature and the solvent was removed the solvent. The crude product was purified by SGC(EtO Ac/Petroleum : 1/1) to afford 79 mg (34%) of 122 as a white solid. 1H NMR (400MHz,CDCl3): delta 9.12 (s, 1 H), 7.98 (s, 1 H), 7.75 – 7.82 (m, 2 H), 7.44 – 7.47 (m, 1 H), 7.08 – 7.09 (m, 1 H), 2.67 (s, 3 H). ESI MS m/z = 229 (M+l)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,929617-30-1, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; LEE, Wendy; TSUI, Vickie Hsiao-Wei; WANG, Xiaojing; WEN, Zhaoyang; WO2013/24002; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20511-12-0 ,Some common heterocyclic compound, 20511-12-0, molecular formula is C5H5IN2, 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.

To a solution of 5-iodopyridin-2-amine(0.7 g, 3.18 mmol) in HBr [(1.26 g, 15.6 mmol (48% in water)] at 0 00 sodium nitrite (0.746 g, 10.82 mmol) in water was added drop wise, followed by addition of bromine (1 .71 g, 10.82 mmol). The reaction mixture was kept at room temperature for 1 h. The reaction mixture was quenched with NaOH solution and extracted with ethyl acetate, washed with water, and dried overanhydrous Na2SO4. The solvent was removed under vacuo. The crude product was purified by column chromatography to yield title compound (0.6 g, 65.23%) as a white solid. LCMS: (M+H) = 284; 1H NMR: (DMSO-d6, 300MHz) 6 8.64-8.65 (d, 1 H), 8.09- 8.12 (dd, 1H), 7.50-7.53 (m, 1H).

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. 20511-12-0, 5-Iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1097264-89-5, name is 2-Chloro-5-fluoro-3-methoxypyridine, molecular formula is C6H5ClFNO, 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. Product Details of 1097264-89-5

To a solution of 2-chloro-5-fluoro-3-(methyloxy)pyridine D47 (0.11 g, 0.70 mmol) in dry toluene (3 ml), sodium t-butoxide (0.094 g, 0.98 mmol), Pd2(dba)3 (0.064 g, 0.07 mmol), BINAP (0.131 g, 0.21 mmol) and benzophenone imine (0.14 ml, 0.84 mmol) were added. The resulting mixture was degassed (3×pump/N2) and then heated to 80 C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (80 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (8 ml) and HCl (0.35 ml of a 2 M aqueous solution, 0.70 mmol) was added. The mixture was stirred at room temperature for 1.5 h, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (40 ml). The phases were separated and the aqueous one back-extracted with DCM (2×10 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M, Cy/EtOAc 60/40) to give the title compound D48 (0.071 g, 0.49 mmol, 70% yield from D47, two steps) as a yellow solid. UPLC: rt=0.28 min, peak observed: 143 (M+1). C6H7FN2O requires 142.

With the rapid development of chemical substances, we look forward to future research findings about 1097264-89-5.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine. A new synthetic method of this compound is introduced below.

General procedure: TCP A (333 mg), complex (1.71 mol%) and solvent (3 mL) are added to each reactor, followed byNEt3 (446 microL). The reactor is purged with nitrogen (3 times) and hydrogen (3 times) thenhydrogenated at 5 bar and various reactor temperatures for 60 mins in a Biotage Endeavor. 40 pL aliquot of each reaction mixture is added to 1 mL MeCN and analysed by normal HPLC method. HPLC areas are converted to concentration (pmol/mL) from the gradients equations in the multipoint external standard.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6515-09-9, 2,3,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; JOHNSON MATTHEY PUBLIC LIMITED COMPANY; MORTIMER, Danny Lee; (19 pag.)WO2017/85476; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 108118-69-0, 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.108118-69-0, name is 2,6-Difluoropyridin-3-amine, molecular formula is C5H4F2N2, molecular weight is 130.0955, as common compound, the synthetic route is as follows.

Synthesis of N-(2,6-difluoropyridin-3-yl)formamide Acetic anhydride (6 ml) was added to formic acid (6 ml), followed by stirring at room temperature for 20 minutes. Then, a solution of 2,6-difluoro-3-aminopyridine (2.06 g) in tert-butyl methyl ether (7 ml) was added so that the reaction solution was maintained at room temperature. The reaction solution was further stirred at room temperature for four hours. Ethyl acetate and a saturated sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.42 g). The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 6.86 (dd, J=8.8, 2.8Hz, 1H), 7.42 (brs, 1H), 8.49 (s, 1H), 8.83-8.90 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 108118-69-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 116026-95-0 ,Some common heterocyclic compound, 116026-95-0, molecular formula is C11H14N2O3, 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.

2-oxo-1,2-Dihydro-[1,7]naphthyridine-3-carboxylic Acid Ethyl Ester (6-3) A solution of 6-2 (2.20 g, 9.90 mmol, 1 equiv), diethyl malonate (3.00 mL, 19.8 mmol, 2.00 equiv), and piperidine (0.490 mL, 4.95 mmol, 0.500 equiv) in ethanol (50 mL) was heated at reflux for 20 h. The reaction mixture was allowed to cool to 23 C., then concentrated to about half its volume. The white crystals which formed were filtered and washed with cold ethanol (20 mL) to give 2-oxo-1,2-dihydro-[1,7]naphthyridine-3-carboxylic acid ethyl ester (6-3). 1H NMR (400 MHz, CDCl3) delta 12.15 (br s, 1H), 8.94 (s, 1H), 8.52 (d, 1H, J=5.2 Hz), 8.46 (s, 1H), 7.52 (d, 1H, J=5.2 Hz), 4.48 (q, 2H, J=7.1 Hz), 1.46 (t, 3H, J=7.1 Hz); TLC (EtOAc), Rf=0.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116026-95-0, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6479512; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1089330-68-6, 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.1089330-68-6, name is 5-Methyl-3-nitropicolinonitrile, molecular formula is C7H5N3O2, molecular weight is 163.13, as common compound, the synthetic route is as follows.

[00261] To acetic acid (300 ml_) in a 3-neck 2 liter round bottom flask equipped with mechanical stirrer and a thermometer was added Fe powder (99.6 g, 1.78 mol) with stirring at 60 0C. 2-Cyano-5-methyl-3- nitropyridine (97 g, 0.59 mol) was dissolved in acetic acid (400 ml_) with gentle warming and added to the above reaction mixture drop wise with efficient stirring so that the reaction temperature kept below 80 “C over 3.5 hours. The reaction mixture was further stirred for an addition 30 min, cooled, diluted with EtOAc (750 ml_), filtered through celite and washed with EtOAc (1 x 500 ml_, 3 x 250 ml_). Combined EtOAc layers were evaporated to dryness to obtain dark brown solid which was neutralized with saturated NaHCO3 solution (850 ml_), after addition of water (250 ml_) to obtain homogeneous, this aqueous layer was extracted with EtOAc (1 x 750 mL, 2 x 500 mL). Combined EtOAc layers were filtered through small pad of silica gel (sand-SiO2-sand in sintered funnel), dried (Na2SO4) and evaporated to obtain 3-amino-2-cyano-5-methylpyridine (60 g) as yellow solid in 76% yield including -10% corresponding amide.[00262] To the crude 3-amino-2-cyano-5-methylpyridine (containing~10% carboxamide) (49 g) was added EtOAc (441 mL, 9: 1 volume ratio to aniline), the resulting suspension was heated to reflux to form a clean solution. After cooling to room temperature, the resulting crystal was collected by filtration, washed with small amount of cold EtOAc (44 mL (1/10 the initial volume) X 2), and dried in vacuo to afford the pure 3-amino-2-cyano-5- methylpyridine (35 g) as pale yellow needles. The mother liquor was concentrated under reduced pressure, the resulting yellow solid was added EtOAc (136 mL) and repeated the above process to afford another 4 g of pure 3-amino-2-cyano-5-methylpyridine; total recovery yield 79.5%. 1H NMR (400 MHz, CDCI3) delta 7.89 (1 H, s), 6.90 (1 H, s), 4.39 (2H, br), 2.30 (3H, s). MS (ES) M+H expect 134.0, found 134.0.

The chemical industry reduces the impact on the environment during synthesis 1089330-68-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2546-56-7, 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. 2546-56-7, name is 4-Chloro-3-fluoropyridine, molecular formula is C5H3ClFN, 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.

Step 1: 2-bromo-4-chloro-3-fluoropyridine 21-l To a solution of 2,2,6,6-tetramethylpiperidine (25g, 190mmol) in hexanes (100 mL) cooled over dry ice acetone bath for 5 minutes was added 1.6M n-butyl lithium in hexanes (121 mL, 194 mmol) over 5 minutes. After the addition was complete, the reaction mixture was placed in an ice bath and the mixture was allowed to stir at 0C for 20 minutes as a white solid formed. The suspension was re-cooled over dry ice/acetone bath for 5 minutes and then treated with a solution of 4-chloro-3-fluoropyridine (25 g, 190 mmol) in hexanes (50 mL) over 5 minutes and this mixture was stirred over dry ice/acetone bath for additional 10 minutes. After this time, this mixture was treated with bromine (30.4 mL, 190 mmol) and stirred over dry ice/acetone bath for 15 minutes. After this time, the reaction mixture was stirred for 30 minutes at O0C and then allowed to warm to room temperature. The reaction mixture was re-cooled over wet ice bath and quenched with water (200 mL) and extracted with ether (3×300 mL). The combined organic extracts were washed with water, dried (MgSO-J.), and the solvent removed in vacuo. The residue was purified by chromatography using 33Og silica gel cartridge and eluting with a gradient of 20-100% CH2CI2 in hexanes to provide the title compound. lH NMR (CDCI3) delta=8.13 (d, IH, J=5.1Hz) and 7.35 (dd, IH, J= 5Hz) ppm.

According to the analysis of related databases, 2546-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/67166; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 915107-31-2, name is Methyl 6-chloro-5-methoxynicotinate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 915107-31-2

To a solution of 6-chloro-5-methoxynicotinic acid methyl ester (1.3 g, 6.4 mmol) in MeOH (4 mL) at 25 C. was added 10% NaOH aqueous solution (19.3 mmol). The reaction was stirred for 24 h, then placed into an ice water bath and acidified with 2M HCl until pH=2 was achieved. The flask was then placed into a refrigerator for 3 h. The white precipitate was filtered off and rinsed with cold H2O. The solid was dissolved in acetone, dried over MgSO4 and concentrated to furnish the product 6-chloro-5-methoxynicotinic acid as a yellow solid (0.895 g, 74%); 1H NMR (400 MHz, CDCl3) delta 8.45 (d, 1H), 7.66 (d, 1H), 3.83 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 915107-31-2, Methyl 6-chloro-5-methoxynicotinate.

Reference:
Patent; Zhu, Yuanming; Loso, Michael R.; Nugent, Benjamin M.; Huang, Jim X.; Rogers, Richard B.; US2008/108667; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75806-86-9 ,Some common heterocyclic compound, 75806-86-9, molecular formula is C5H2BrClN2O2, 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 mixture of 2-bromo-5-chloro-3-nitropyridine (2.8 g; 11.79 mmol) and copper(I) cyanide (1.40 g, 15.63 mmol) in DMF (30 mL)was stirred at 110C for 1.5 h. The mixture was concentrated. The residue was diluted with water (60 mL), extracted three times with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by columnchromatography (elution: DCM/Petroleum ether 1/1). The desired fractions were collected and concentrated to give 1.10 g of intermediate 521 (51% yield) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-86-9, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem