1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol → 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

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Reaction Steps

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol (Example 68) (0.65 g, 4.0 mmol) in THF (80 mL) was added manganese dioxide (4.18 g, 48 mmol). After stirring 2 h at room temperature, TLC analysis indicated that the reaction was completed. The reaction mixture was filtered through diatomaceous earth and rinsed with EtOAc. The filtrate was concentrated and triturated with Et2O to provide 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone as an off-white solid: mp 236-242° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.63 (3H, s), 7.34 (1H, s), 7.70-7.73 (1H, m), 8.13 (1H, d, J=5.7 Hz), 8.80 (1H, s); ESI MS m/z 161 [C9H8N2O+H]+; HPLC (Method A) 92.7% (AUC), tR=7.75 min.

Provenance & Evidence