Skatole → HCID 9794477, compound

Participants

Reaction Steps

The above general procedure was followed using 2-bromotoluene (205 mg, 1.20 mmol), 3-methylindole (131 mg, 1.00 mmol), 3 mo % Pd(dba)2, 2.4 mol % tri-t-butylphosphine, and cesium carbonate (1.70 mmol) in 1.0 mL of toluene. After 12 hours at 100° C., the reaction mixture was adsorbed onto silica gel and chromatographed with 5% ethyl acetate/hexanes to give 195 mg (88%) of N-(2-methylphenyl)-3-methylindole. 1H NMR (300 MHz, CDCl3) δ 7.76 (m, 1H), 7.46 (m, 2H), 7.40 (m, 2H), 7.28 (m, 2H), 7.15 (m, 1H), 7.06 (s, 1H), 2.53 (S, 3H), 2.21 (s, 3H). 13C NMR (76 MHz, CDCl3) δ 138.4, 137.1, 135.7, 131.1, 128.6, 128.1, 127.8, 126.6, 126.2, 121.9, 119.3, 118.9, 111.6, 110.4, 17.7, 9.6.

Provenance & Evidence