Acetic Acid → 3-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine

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Reaction Steps

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine (Intermediate 10.1) (150.0 mg, 0.57 mmol), glacial acetic acid (39.3 μl, 0.69 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (175.4 mg, 0.91 mmol), 4-dimethylaminopyridine 419.2 mg, 3.43 mmol), and dichloromethane (10 ml) is stirred for 24 h at ambient temperature. The mixture is successively extracted with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate. The organic layer is dried over sodium sulfate and concentrated in vacuo to render 139.1 mg (80%) of the respective amide. HPLC (over 10 min 10-85% MeCN/100 mM aq. NaOAc): 99% purity, tR 6.43 min (tR(SM) 6.64 min). GC/MS: 96% purity, tR 13.98 min, m/z 304 (M, 58), 262 (100), 207 (62) Finnegan LCQ.

Provenance & Evidence