1,2-Dichloroethane → 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-(1-methylethyl)-1H-indole-7-carboxamide

Participants

Reaction Steps

To a stirred suspension of 5-bromo-3-(1-methylethyl)-1H-indole-7-carboxylic acid (400 mg, 1.418 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (300 mg, 1.590 mmol) and HOAt (220 mg, 1.616 mmol) in DMF (15 mL) was added N-methylmorpholine (180 μL, 1.637 mmol) and EDC free base (330 mg, 2.127 mmol). The reaction was stirred for 18 h at RT. LCMS showed that the reaction was complete. The reaction was evaporated to near dryness under vacuum. Water (˜15 mL) was added and the solids which precipitated out were triturated, filtered and dried under vacuum to give 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-(1-methylethyl)-1H-indole-7-carboxamide (571 mg, 1.372 mmol, 97% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (br. s., 1H), 11.03 (br. s., 1H), 8.58 (t, J=4.55 Hz, 1H), 7.85 (d, J=1.26 Hz, 1H), 7.82 (s, 1H), 7.12 (d, J=2.02 Hz, 1H), 5.89 (s, 1H), 4.35 (d, J=4.55 Hz, 2H), 3.13 (ddd, J=6.57, 6.69, 13.52 Hz, 1H), 2.20 (s, 3H), 2.13 (s, 3H), 1.27 (d, J=6.82 Hz, 6H). MS (ES) [M+H]+ 415.9, 418.0.

Provenance & Evidence