Tag: M.W:100-200

Application of 60753-14-2 ,Some common heterocyclic compound, 60753-14-2, molecular formula is C9H13NO, 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: To a solution of 3-(pyridin-4-yl)propan-1-ol (151mg, 1.1mmol), 2-(3-bromophenylthio)pyridine-3-ol (5) (282mg 1.0mmol) and triphenylphosphine (289mg, 1.1mmol) in THF (2.0mL) was added diisopropylazodicarboxylate (222mg 1.1mmol) at 0C and stirred at ambient temperature. After 5h, the mixture was evaporated, diluted with EtOAc (15mL), and extracted with 10% HCl solution (2×15mL). The aqueous phase was then basified to pH 12 with K2CO3 and extracted with EtOAc (2×15mL). The organic phase was washed with brine (2×5mL), dried (Na2SO4), and evaporated in vacuo. The residue was subjected to flash column chromatography (EtOAc-hexane gradient) followed by crystallization (Et2O) to afford title compound 3 as a white crystalline solid (390mg, 97%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60753-14-2, its application will become more common.

Reference:
Article; Kato, Yoshihiro; Kawasaki, Motoji; Nigo, Tomohiro; Nakamura, Shunya; Fusano, Akira; Teranishi, Yasuhiro; Ito, Mari N.; Sumiyoshi, Takaaki; Bioorganic and Medicinal Chemistry; vol. 21; 18; (2013); p. 5851 – 5854;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65873-72-5, 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.65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.

Reference Example 28Step 15-chloromethyl-2-methoxypyridine (Compound A80)2-methoxy-5-pyridinecarbaldehyde (137 mg, 0.999 mmol) was dissolved in methanol (5.0mL). To this, sodium borohydride (37.8 mg, 0.999 mmol) was added at 0C, and the mixture was stirred for 1 hour. To the reaction mixture, a saturated ammonium chloride aqueous solution was added, and extraction with ethyl acetate was performed twice. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was dissolved in dichloromethane (5.0 mL). To this, triethylamine (278 muL, 2.00 mmol) and methanesulfonyl chloride (116 muL, 1.50 mmol) were added, and the mixture was stirred overnight. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, extraction with chloroform was performed twice. The organic layer was dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography to give Compound A80 (116 mg, yield: 74%). ESI-MS: m/z 158 [M + H]+; 1H NMR (CDCl3)delta(ppm): 3.94 (s, 3H), 4.55 (s, 2H), 6.76 (d, J = 8.4 Hz, 1H), 7.62 (dd, J = 2.4, 8.4 Hz, 1H), 8.15 (d, J = 2.4 Hz, 1H).

Statistics shows that 65873-72-5 is playing an increasingly important role. we look forward to future research findings about 6-Methoxynicotinaldehyde.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2308880; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1033203-41-6, 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.1033203-41-6, name is 6-Bromopyridine-3,4-diamine, molecular formula is C5H6BrN3, molecular weight is 188.0252, as common compound, the synthetic route is as follows.

0.85 g (4.5 mmol) of Compound 22-1 and 0.34 g (4 mmol) of Compound 22-2 were added to 15 mL of ethanol solution in an N2 atmosphere and heated to undergo a reaction for 5 hours. After the reaction was completed, a residue obtained therefrom was separated and purified by column chromatography (petroleum ether:ethyl acetate=12:1) to obtain 0.71 g (yield: 75%) of Compound 22-3.

Statistics shows that 1033203-41-6 is playing an increasingly important role. we look forward to future research findings about 6-Bromopyridine-3,4-diamine.

Reference:
Patent; Samsung Display Co., Ltd.; YOO, Byeongwook; KIM, Myeongsuk; YE, Jimyoung; KIM, Hyoyeon; YOON, Jihwan; HWANG, Jaehoon; (72 pag.)US2019/218240; (2019); 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

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

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

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

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

Application of 81803-60-3, 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.81803-60-3, name is Ethyl imidazo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

Under hydrogen a solution of ethyl imidazo[1,5-a]pyridine-3-carboxylate (300 mg, 1.58 mmol,1.00 equiv) and Pd/C (10 wt%, 30 mg) in methanol (20 mL) was stirred for 30 h at room temperature. After filtration the filtrate was collected and concentrated under vacuum. This resulted in 325 mg of the title compound (crude) as a white solid. LC-MS (ES, mlz): 195 [M+H].

The chemical industry reduces the impact on the environment during synthesis 81803-60-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 67310-56-9, Adding some certain compound to certain chemical reactions, such as: 67310-56-9, name is 1-(5-Hydroxypyridin-2-yl)ethanone,molecular formula is C7H7NO2, 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 67310-56-9.

A 2.5 mL microwave vial was charged with Example 28A (35 mg, 1 equivalent, 0.096 mmol), K2CO3(27mg, 0.19 mmol), l-(5-hydroxypyridin-2-yl)ethanone (27 mg, 0.19 mmol) and potassium iodide (1,2 mg, 0.07 equivalent, 0.05 mmol). To this mixture was added acetone (1.5 mL). The resulting mixture was heated in a Biotage Initiator microwave for 45 minutes at 140 C (0-450 W). Upon completion, the mixture was then filtered, and the filtrate was concentrated to dryness. The residue was dissolved in 1 : 1 dimethyl sulfoxide/methanol and purified by preparative reverse phase HPLC on a Phenomenex Luna C8(2) 5 mupiiota 100 A AXIA column (30 mm x 150mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 5% A, 0.5-8.5 minutes linear gradient 5- 100% A, 8.7-10.7 minutes 100% A, 10.7 -11.0 minutes linear gradient 100-5% A) to afford the title compound.JH NMR (400 MHz, DMSO- ) delta ppm 8.39 (d, / = 2.9 Hz, 1H), 7.96 (d, / = 8.8 Hz, 1H), 7.53 – 7.45 (m, 2H), 7.05 (dd, / = 11.3, 2.9 Hz, 1H), 6.85 (ddd, / = 9.0, 2.8, 1.2 Hz, 1H), 4.64 (s, 2H), 4.46 (s, 2H), 2.58 (s, 3H), 2.28 (s, 6H). MS (APCI) m/z 462.3 (M+H)+.

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. 67310-56-9, 1-(5-Hydroxypyridin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem