2-Fluorophenylboronic acid → 3-Benzoyl-10-(2-fluorophenyl)-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 (0.738 g, 2.0 mmol) and tetrakis(triphenylphosphine)palladium (0.23 g, 0.20 mmol) in dimethoxyethane (5.0 mL) and a solution of 2-fluorophenylboronic acid (0.336 g, 2.4 mmol) in dimethoxyethane (5.0 mL) and sodium carbonate (2 M, 7.0 mL) were-reacted in a manner similar to Preparation 1. Column chromatography (silica gel, 20-50% EtOAc/heptane) afforded 0.33 g (43%) of the title compound as a solid: mp 241-244° C.; 1H NMR (400 MHz, CDCl3) δ 8.20, 8.04, 7.31, 7.15, 7.04, 3.96, 3.83, 3.62, 3.42, 3.14, 2.84, 2.71-2.69, 2.47, 2.31; IR (drift) 3236, 1603, 1501, 1485, 1469, 1456, 1434, 1249, 1217, 795, 786, 759, 746, 733, 706 cm−1; MS (EI) m/z 384 (M+); HRMS (FAB) calcd for C25H21FN2O+H: 385.1716, found: 385.1721; Anal. Calcd for C25H21FN2O: C, 78.10; H, 5.51; N, 7.29. Found: C, 77.61; H, 5.60; N, 7.14.

Provenance & Evidence