Potassium Carbonate → 3-Benzoyl-10-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Participants

Reaction Steps

A mixture of 3-benzoyl-10-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.517 g, 1.40 mmol), potassium carbonate (0.77 g, 5.60 mmol), phenylboronic acid (0.194 g, 1.54 mmol), tetrakis(triphenylphosphine)palladium (0.16 g, 0.14 mmol) in tetrahydrofuran (7.0 mL) and N,N-dimethylacetamide (7.0 mL) reacted in a manner similar to Preparation 1. Column chromatography (silica gel, 10-50% EtOAc/heptane) afforded 0.49 g (95%) of the title compound as a solid: mp 223-226° C.; 1H NMR (400 MHz, CDCl3) δ 8.25, 7.57-7.23, 7.18-7.12, 6.98-6.89, 4.02-3.93, 3.76-3.67, 3.65-3.56, 3.43-3.35, 3.18-3.12, 2.90-2.83, 2.66-2.58, 2.43-2.34; IR (drift) 3231, 3203, 1602, 1501, 1468, 1433, 1352, 1336, 1249, 786, 758, 746, 740, 706, 700 cm−1; MS (EI) m/z 366 (M+); Anal. Calcd for C25H22N2O: C, 81.94; H, 6.05; N, 7.64. Found: C, 81.75; H, 6.07; N, 7.61.

Provenance & Evidence