2,5-Dimethylaniline → HCID 57857515, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure A, a mixture of 4-(1H-pyrrol-1-yl)phenylmethanesulfonate (119 mg, 0.5 mmol), 2,5-dimethylaniline (75 μL, 0.6 mmol), K2CO3 (97 mg, 0.7 mmol), 10 (4 mg, 1 mol %), 1 (2.5 mg, 1 mol %), and t-BuOH (6 mL) was heated to 110° C. for 16 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes) to provide the title compound as a white solid (138 mg, 95%), mp 97-98° C. 1H NMR (300 MHz, CDCl3) δ: 7.31 (d, J=9.0 Hz, 2H), 7.14 (d, J=7.5 Hz, 1H), 7.04 (m, 5H), 6.82 (d, J=7.5 Hz, 1H), 6.37 (t, J=2.5 Hz, 2H), 5.40 (s, 1H), 2.33 (s, 3H), 2.27 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 142.4, 141.1, 136.9, 134.4, 131.2, 125.6, 123.3, 122.3, 119.9, 119.8, 118.5, 110.0, 21.5, 17.8 ppm. IR (neat, cm−1): 3386, 2920, 1519, 1310, 1072, 829, 726. Anal. Calcd. for C18H18N2: C, 82.41; H, 6.92. Found: C, 82.03; H, 7.03.

Provenance & Evidence