(5-Fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol → 1H-Pyrrolo[2,3-b]pyridine-4-carboxaldehyde, 5-fluoro-

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask equipped with a stirring bar was added (5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol (2.01 g, 12.10 mmol) in THF (100 mL) under nitrogen. Manganese dioxide (10.52 g, 121 mmol) was added and the reaction mixture was stirred at 60° C. for 2 h. The organics were filtered through a pad of Celite, rinsed with EtOAc (100 mL) and concentrated. The resulting solid was triturated with EtOAc (50 mL) and filtered to give the title compound as a light yellow solid (1.3 g, 65.5%). 1H NMR (400 MHz, CD3OD) δ 4.59 (s, 1 H) 5.34 (d, J=3.54 Hz, 1 H) 5.86-6.08 (m, 1 H) 6.58 (d, J=3.28 Hz, 1 H). [M+H] calc'd for C8H5FN2O, 165; found, 165.5.

Provenance & Evidence