Ethyl Bromide → 1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-fluoro-1H-pyrrolo[2,3-b]pyridine (15.00 g, 110.19 mmol) in DMF (100 mL), under a nitrogen atmosphere, is added potassium carbonate (22.84 g, 165.3 mmol), followed by ethyl bromide (12.36 mL, 165.3 mmol). The reaction is heated to 70° C. for 4 h. Further ethyl bromide (3.00 mL, 27.6 mmol) is added and the reaction kept at 70° C. overnight. After cooling further potassium carbonate (8.00 g, 57.9 mmol) and ethyl bromide (3.00 mL, 27.6 mmol) are added, and the reaction heated at 70° C. for 4 h. The reaction is cooled, poured onto brine (ca. 500 mL) and the product extracted with CHCl3 (ca. 2×300 mL). The combined organic extracts are dried over magnesium sulphate, filtered, and concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 70% DCM in hexane to give the title compound as a light yellow oil (16.38 g, 99.77 mmol). MS (m/z): 165 (M+1).

Provenance & Evidence