Aluminum(III) Chloride → HCID 69199550, compound

Participants

Reaction Steps

To a stirred solution of ethyl 1-(4-fluorobenzyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (4.0 g, 13.4 mmol) in dichloromethane (60 mL) were added aluminum chloride (3.6 g, 26.8 mmol) and 4-fluorobenzoyl bromide (3.2 mL, 26.8 mmol). The resulting mixture was stirred for three days at ambient temperature. It was quenched with ice-water (100 mL), and extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with water (2×100 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Elution with hexane:ethyl acetate (1:1) provided the title compound as a solid (2.2 g, 39% yield). 1H NMR (CDCl3) δ ppm 9.62 (s, 1H), 8.23 (s, 1H), 7.85-7.87 (m, 2H), 7.74 (s, 1H), 7.12-7.18 (m, 4H), 7.03-7.06 (m, 2H), 5.43 (s, 2H), 4.51 (q, 2H, J=7.2 Hz), 1.47 (t, 3H, J=7.2 Hz). LCMS (APCI, M+H+): 421.1.

Provenance & Evidence