Dichloromethane → HCID 22396573, compound

Participants

Reaction Steps

tert-Butyl 10-(2,6-difluorophenyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.700 g, 1.76 mmol) was dissolved in CF3CO2H (4 mL) and CH2Cl2 (14 mL) and the reaction mixture was stirred at rt for 3 h. The reaction mixture was cooled in an ice bath and quenched with cold 1N NaOH (100 mL). The resulting mixture was extracted with 3% CH3OH in CH2Cl2 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product (0.51 g) was chromatographed (SiO2 30 g, eluted with 90:10:1 CH2Cl2:CH3OH:conc. NH4OH) to yield 10-(2,6-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.458 g) in 87% yield. 1H NMR (400 MHz, Acetone-d6) δ 2.35-2.38, 2.74-2.77, 2.95-2.98, 6.84, 7.08, 7.12, 7.36, 7.50; MS (ESI+) for C18H16F2N2 m/z 299.1 (M+H)+.

Provenance & Evidence