Phenol → N-(7-phenoxyisoquinolin-3-yl)cyclopropanecarboxamide

Participants

Reaction Steps

N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (89 mg, 0.30 mmol), phenol (86.5 mg, 0.92 mmol, 3 eq), 3, 4,7,8-tetramethyl-1,10-phenanthrolin (35.4 mg, 0.15 mmol, 0.5 eq), copper(I) iodide (57.3 mg, 0.3 mmol, 1 eq) and cesium carbonate (293.2 mg, 0.9 mmol, 3 eq) in 1-methyl-2-pyrrolidinone (2.5 ml) were stirred under microwave irradiation at 180° C. for 99 min under nitrogen. The mixture was diluted with dichloromethane and filtered through a pad of Celite. The filer cake was washed with dichloromethane and the combined filtrate was concentrated and purified by prep-HPLC to give product (30 mg, 26%). LCMS (ESI): RT (min)=1.107, M+H+=305.0, method=A. 1H NMR (400 MHz, CDCl3) δ 8.76 (s, 1H), 8.46 (s, 1H), 8.24 (s, 1H), 7.72 (d, J=9.2 Hz, 1H), 7.38-7.00 (m, 5H), 1.55-1.52 (m, 1H), 1.10-1.06 (m, 2H), 0.87-0.82 (m, 2H).

Provenance & Evidence