2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol → 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone

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Reaction Steps

2-Methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol (Example 78) (75 mg, 0.39 mmol) was dissolved in methylene chloride (10 mL). Manganese dioxide (343 mg, 3.94 mmol) was added and the reaction mixture was stirred for ca. 14 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with hot methanol. The filtrate was concentrated to give a white solid. Drying under vacuum produced 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone (64 mg, 88%) as a white solid: mp 224-228° C.; 1H NMR (500 MHz, CD3OD) δ1.26 (6H, d, J=7.0 Hz), 3.45-3.62 (1H, m), 7.37 (1H, s), 7.72-7.74 (1H, m), 8.14 (1H, d, J=6.0 Hz), 8.82 (1H, s); ESI MS m/z 189 [C11H12N2O+H]+; HPLC (Method A) 95.4% (AUC), tR=13.7 min.

Provenance & Evidence