1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-phenyl-1-(phenylsulfonyl)- → 1h-Pyrrolo[2,3-c]pyridine,2-benzoyl-1-(phenylsulfonyl)-

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Reaction Steps

A mixture of phenyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (2.6 g, 7.1 mmol) and MnO2 (9.3 g, 110 mmol) in THF (125 mL) was heated to reflux. After 20 h, the reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure. Purification by column chromatography (silica gel, CH2Cl2 to 99:1 CH2Cl2/MeOH) gave phenyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanone (1.7 g, 68%) as an off-white solid: mp 145-146° C.; 1H NMR (500 MHz, DMSO-d6) δ7.32 (1H, s), 7.60-7.63 (2H, m), 7.66-7.69 (2H, m), 7.73-7.77 (3H, m), 7.93-7.95 (2H, m), 8.07-8.09 (2H, m), 8.50 (1H, d, J=5.3 Hz), 9.35 (1H, s); ESI MS m/z 363 [C20H14N2O3S+H]+; HPLC (Method A) 99.0% (AUC), tR=18.2 min.

Provenance & Evidence