Methyl iodide → 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (207 mg, 1.05 mmol), sodium hydride (29 mg, 1.21 mmol) in tetrahydrofuran (5 mL) was added iodomethane (164 mg, 1.15 mol) then stirred for 2 h at room temperature. The reaction mixture was carefully quenched with water then extracted with ethyl acetate (3×). The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to give 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine. MS (EI) for C8H7BrN2: 209, 211 (MH+, Br pattern).

Provenance & Evidence