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

Participants

Reaction Steps

To a stirred suspension of 1-methyl-3-(1-methylethyl)-5-(methyloxy)-1H-indole-7-carboxylic acid (78 mg, 0.315 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (59.5 mg, 0.315 mmol), HOAt (64 mg, 0.473 mmol) in DMF (4 mL) was added EDC (121 mg, 0.631 mmol) and N-methylmorpholine (52 μL, 0.473 mmol). The reaction mixture was stirred for 18 hr at room temperature, after which time the contents were evaporated to near dryness. Water (˜5 mL) was added and the solids which precipitated out were isolated. The collected solid was dissolved in DCM/MeOH (4:1, 5 mL), dried over MgSO4, filtered, and concentrated in vacuo to a afford a creme colored solid. The solid was re-dissolved in DCM/MeOH (4:1, 5 mL) and washed with 6N NaOH (1 mL) and water (4 mL). The organic layer was concentrated in vacuo to afford a nearly white solid.

Provenance & Evidence