Carbon Tetrachloride → tert-Butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (270 mg, 1.09 mmol) in 2.5 mL DMF was added triphenylphospine (285 mg, 1.09 mmol) and carbon tetrachloride (167 mg, 1.09 mmol). The reaction was allowed to stir 16 h at ambient temperature. The solution was concentrated and purified by silica gel chromatography (0-50% ethylacetate/hexanes) to give tert-butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (8.6%). 1H NMR (400 MHz, CDCl3): δ 8.56-8.55 (d, J=4.9 Hz, 1H), 8.02-8.00 (d, J=8.1 Hz, 1H), 7.69 (s, 1H), 7.26-7.24 (m, 1H), 5.30 (s, 2H), 1.54 (s, 9H).

Provenance & Evidence