1,2-Dichloroethane → 1H-Indole-2-carboxamide

Participants

Reaction Steps

To intermediate 34 G (102.9 mg, 0.24 mmol) in DCM (5 mL) was added 2-indole carboxylic acid (47 mg, 0.29 mmol), HOBT (39 mg, 0.29 mmol), EDC (56 mg, 0.29 mmol) and 2d triethylamine. The reaction mixture was stirred for 16 h, diluted with EtOAc (100 mL), washed with saturated NaHCO3 (2×20 mL), 1N aqueous HCl (2×20 mL), brine (1×20 mL), dried (MgSO4), and concentrated to give the indole amide (110 mg, 80%). Rf =0.58 (10% methanol/DCM); 1HNMR (300 MHz, CDCl3) d 1.04 (d, J=6.8 Hz, 3H), 1.06 (d, J=6.8 Hz, 3H), 1,39 (s, 6H), 3.58 (d, J=16.6 Hz, 1H), 3.83 (s, 3H), 4.59 (d, J=16.6 Hz, 1H), 4.76 (d, J=8.5 Hz, 1H), 5.03 (m, 1H), 6.89 (m, 2H), 6.98 (m, 3H), 7.13 (m, 2H), 7.45 (m, 3H), 7.61 (m, 2H), 8.98 (s, 1H); MS(FAB) m/z 571.2 (MH+).

Provenance & Evidence