4-Hydroxymethylpyridine → 3-bromo-1-methyl-6-(pyridin-4-ylmethoxy)-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a solution of 3-bromo-6-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine (0.4 g, 1.74 mmol) and pyridine-4-ylmethanol (0.21 g, 1.93 mmol) in DMF (5.0 mL) is added portionwise sodium hydride (0.05 g, 2.11 mmol) at room temperature and the resulting reaction mixture is stirred for 1 h. The reaction is quenched with cold brine solution and extracted with EtOAc (4×100 mL). The combined organic layers are dried over sodium sulphate, filtered and concentrated in vacuo. The residue is purified by crystallization from Et2O/pentane to give the title compound (0.300 g, 0.942 mmol) as an orange-red solid. MS (m/z): 318, 320 (M+1). 1H-NMR (400 MHz, DMSO-d6): δ 3.73 (s, 3H), 5.48 (s, 2H), 6.76 (d, 1H), 7.47 (d, 2H), 7.50 (s, 1H), 7.78 (d, 1H), 8.56 (d, 2H).

Provenance & Evidence