Related Products of 90145-48-5 ,Some common heterocyclic compound, 90145-48-5, molecular formula is C6H5BrN2O, 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.
Example 5Preparation of 5-bromo-N-(1 -(4-chlorophenylamino)-2-(naphthalen-1 -yl)-2- oxoethvDpicolinamide (Compound-1 )[0098] A mixture of 5-bromopicolinamide 111 (0.588 g, 2.92 mmol) and 2,2- dihydroxy-1 -(naphthalen-1 -yl)ethanone 112 (1 .20 g, 5.67 mmol) in dioxane (20 mL) were heated at 100 C for 18 hours. The dioxane was removed under vacuum and the residue was dissolved in chloroform and methanol and concentrated onto silica gel. The material was purified by auto flash system (CH2CI2 to 1 % MeOH: CH2CI2) to give 5-bromo-N-(1 -hydroxy-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide 113 as a tan solid (0.74 g, 66%). [0099] 5-bromo-N-(1 -hydroxy-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide 113 (0.74 g, 1.93 mmol) in chloroform (20 mL) was reacted with PCI5 (0.43 g, 1.96 mmol). The mixture was heated to 50 C for 30 minutes and cooled to 0 C. 4-Chloroaniline 114 (0.512 g, 4.01 mmol) in THF (10 mL) was added and allowed to react for 1 hour. The reaction was quenched with water and the product was extracted with ethyl acetate. The organic solution was dried over MgS04, filtered and concentrated onto silica gel. The product was purified by auto flash column chromatography (30 to 50% CH2CI2: hexane) followed by titration with diethyl ether to give 5-bromo-N-(1-(4- chlorophenylamino)-2-(naphthalen-1-yl)-2-oxoethyl)picolinamide (Compound-1 , 352 mg, 37%). 1H NMR (300 MHz, CDCI3): delta = 8.83 (d, J = 8.7 Hz, 1H), 8.50 (d, J= 1.5 Hz, 1H), 8.46 (d, J = 9.6 Hz, 1H), 8.39 (dd, J = 1.2, 7.2 Hz, 1H), 8.07-8.03 (m, 2H), 7.93 (dd, J = 2.4, 8.7 Hz, 1 H), 7.89 (d, J = 7.5 Hz, 1 H), 7.68-7.63 (m, 1 H), 7.56 (t, J = 7.8 Hz, 2H), 7.16 (d, J = 8.7 Hz, 2H), 7.09-7.03 (m, 1H), 6.82 (d, J = 9.0 Hz, 2H) 5.41 (d, J= 8.1 Hz, 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. 90145-48-5, 5-Bromopyridine-2-carboxamide, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ALLERGAN, INC.; GARST, Michael E.; CHOW, Ken; HEIDELBAUGH, Todd M.; NGUYEN, Phong; WO2011/28927; (2011); A1;,
Pyridine – Wikipedia,
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