Sodium Methoxide → 5-Bromo-4-methoxy-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.16 mmol) was combined with sodium methoxide (583 mg, 10.8 mmol) and suspended in anhydrous methanol (10 mL). The reaction was heated in the microwave to 175° C. for 4 h. The reaction mixture was concentrated and purified by flash silica gel chromatography using a gradient of (ethyl acetate/methanol 9:1) in hexanes to afford 5-Bromo-4-methoxy-1H-pyrrolo[2,3-b]pyridine (130 mg, 0.57 mmol, 27%) as a light yellow powder. 1H NMR (500 MHz, DMSO-d6) δ 11.84 (bs, 1H), 8.14 (s, 1H), 7.40 (m, 1H), 6.80 (m, 1H), 4.30 (s, 3H). MS: m/z 226.9/228.9 (M+H).

Provenance & Evidence