Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-Methyl-2-phenoxyquinolin-8-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of 8-bromo-3-methyl-2-phenoxyquinoline (505.5 mg, 1.609 mmol), tributyl(1-ethoxyvinyl)stannane (Synthonix, Inc., Wake Forest, N.C.; 0.598 mL, 1.770 mmol), and Pd(PPh3)4 (93 mg, 0.080 mmol) in toluene (8.0 mL) was sparged with argon and then stirred under N2 at 100° C. for 16 h. The mixture was cooled to 25° C. and concentrated onto silica gel. Chromatographic purification (silica gel, 0-20% EtOAc/hexanes) furnished 1-(3-methyl-2-phenoxyquinolin-8-yl)ethanone (326.0 mg, 1.176 mmol, 73% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.95 (1H, s), 7.90 (1H, dd, J=7.2, 1.4 Hz), 7.82 (1H, dd, J=8.0, 1.2 Hz), 7.37-7.47 (3H, m), 7.23-7.25 (1H, m), 7.19 (2H, d, J=8.1 Hz), 2.55 (3H, d, J=0.6 Hz), 2.28 (3H, s). m/z (EST, +ve) 278.1 (M+H)+.

Provenance & Evidence