2-Methylindole → HCID 69300406, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-methylindole (6.23 g, 47.5 mmol), 4-benzyloxy-3-fluoro bromobenzene (14.066 g, 50 mmol), potassium carbonate (5.83 g, 55 mmol), and N-methylpyrrolidinone (500 mL) was added copper (I) bromide (1.0 g, 7 mmol). The stirred solution was heated to 180° C. and maintained for 18 hr. The reaction mixture was cooled, poured onto ice and extracted with ethyl acetate. After washing the organic layer with water and brine, and drying over anhydrous MgSO4 the solvent was removed to yield a dark liquid, which was purified by silica gel chromatography (2% ethyl acetate-hexanes) to provide the title compound alley as a white solid (3.45 gr. 22% yd): mp 70-71° C.; 1H NMR (DMSO-d6): δ 2.26 (3H, s), 5.28 (2H, s), 6.39 (1H, s), 6.99-7.05 (3H, m), 7.21-7.24 (2H, m), 7.36-7.54 (7H, m)); MS m/z (M+H)+332: Anal. for C22H18NOF 0.1H2O: Calc'd: C, 79.31; H, 5.51; N, 4.20. Found: C, 79.29; H, 5.39; N, 4.16

Provenance & Evidence