Electric Literature of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.
b) 4-(Benzyloxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)pyridin-2(1H)-one hydrochloride A suspension of 4-(benzyloxy)pyridin-2(1H)-one (71 mg, 0.35 mmol), tert-butyl 8-bromo-6-tosyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate (202 mg, 0.389 mmol), CuI (81 mg, 0.43 mmol), 8-hydroxyquinoline (62 mg, 0.43 mmol) and Cs2CO3 (127 mg, 0.389 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. The suspension was put under N2 and stirred at 135 C. for 4.5 h. The suspension was cooled, 9:0.9:0.1 CH2Cl2/MeOH/NH4OH (10 mL) was added, and the resulting suspension was stirred at 25 C. for 30 min. The suspension was passed through a plug of silica gel, and the filtrate was washed with brine. The resulting solution was dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded 190 mg of a yellow solid. NaOH (594 mg, 14.8 mmol) was added to a solution of the yellow solid in 1:1 MeOH/CH2Cl2 (20 mL) under N2, and the resulting suspension was stirred at reflux for 16 h. The reaction was cooled, H2O was added, and the resulting suspension was filtered. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded a green solid. Preparative HPLC (Phenomenex Luna C18 (2), 250.0*50.0 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) afforded 50 mg of a white powder. 2 N HCl in Et2O (200 mL) was added to a solution of the white powder in 1:1 CH2Cl2/MeOH (4 mL) under N2, and the resulting suspension was stirred at 25 C. for 18 h. The suspension was filtered, and the solid was washed with Et2O to afford the title compound (35 mg, 23%) as a white solid: mp 258-260 C.; 1H NMR (500 MHz, DMSO-d6) delta 11.18 (s, 1H), 9.06 (br s, 2H), 7.57-7.35 (m, 7H), 7.25 (s, 1H), 6.90 (d, J=8.0 Hz), 6.11-6.07 (m, 1H), 5.96 (s, 1H), 5.15 (s, 2H), 3.45-3.30 (m, 4H), 3.20-3.15 (m, 2H), 3.12-3.06 (m, 2H); ESI MS m/z 386 [M+H]+.
According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.
Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
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