Acetyl chloride → HCID 49869916, compound

Participants

Reaction Conditions

Reaction Steps

AcCl (0.03 mL, 0.4 mmol) was added to a solution of 4-(benzyloxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)pyridin-2(1H)-one hydrochloride (102 mg, 0.242 mmol), DMAP (6 mg, 0.05 mmol) and Et3N (0.10 mL, 0.73 mmol) in CH2Cl2 (10 mL) under N2, and the resulting solution was stirred at 25° C. for 4 h. The solution was concentrated under reduced pressure. Flash chromatography on silica gel (Et2O/(8:1.9:0.1 Et2O/MeOH/NH4OH) afforded 35 mg (34%) of the title compound as an off-white solid: mp 250-254° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.99 (s, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.49-7.35 (m, 6H), 7.19 (dd, J=2.5, 2.5 Hz, 1H), 6.88-6.83 (m, 1H), 6.07 (dd, J=8.0, 2.5 Hz, 1H), 5.95 (d, J=2.5, 1H), 5.14 (s, 2H), 3.76-3.65 (m, 4H), 3.06-3.02 (m, 1H), 2.97-2.91 (m, 2H), 2.87-2.82 (m, 1H), 2.12 (s, 3H); ESI MS m/z 428 [M+H]+.

Provenance & Evidence