Ethyl Acetate → 2-(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)acetamide

Participants

Reaction Steps

To a stirred solution of (1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetic acid (397) (2.7 g, 11.05 mmol) in dimethylformamide (60 mL) was added N,N-diisopropylethylamine (5.8 mL, 33.16 mmol) followed by (NH4)2CO3 (5.2 g, 33.16 mmol) and HATU (6.3 g, 16.58 mmol) and stirring was continued for 1 h at room temperature (TLC, 50% ethyl acetate in hexane, Rf=0.5), Water (200 mL) was added and the mixture was extracted with ethyl acetate (2×200 mL), organic part was washed with water (2×100 mL) and brine (2×100 mL). The organic phase was thereafter dried and concentrated. The crude product was purified by Combi-Flash column chromatography (eluted at 30-40% ethyl acetate in hexane) to get 2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)acetamide (398) (1.7 g, 63%) as a yellow solid.

Provenance & Evidence