3,4-Dimethylaniline → HCID 66965792, compound

Participants

Reaction Steps

To a solution of 2-(2,6-dichlorophenyl)-1-ethoxy-1H-indole-6-carboxylic acid (230 mg, 660 μmol) in DMF (5 mL) was added HATU (375 mg, 990 μmol), triethylamine (137 μL, 99 mg, 980 μmol) and 3,4-dimethylaniline (80 mg, 660 μmol). After stirring the mixture for 72 h at ambient temperature, the solution was poured into ethyl acetate and extracted with water once and brine five times. The organic layer was dried, filtered, and solvent removed under reduced pressure. The residual material was chromatographed with a 10-60% gradient of heptane/ethyl acetate to afford 2-(2,6-dichlorophenyl)-1-ethoxy-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide. 1H NMR (DMSO-d6, 400 MHz): δ 10.16 (s, 1H), 8.19 (s, 1H), 7.71 (m, 4H), 7.58 (m, 3H), 7.12 (d, J=8.2 Hz, 1H), 6.60 (s, 1H), 4.14 (q, J=7.1 Hz, 2H), 2.24 (s, 3H), 2.21 (s, 3H), 1.12 (t, J=7.1 Hz, 3H). MS (m/z) 453.0 (M+1); Retention time=1.72 min (Method 10). Anal. Calcd.: C, 66.23; H, 4.89; N, 6.18. Found: C, 66.34; H, 4.97; N, 6.06.

Provenance & Evidence