3-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol → 3-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

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Reaction Steps

3-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (130 mg, 0.61 mmol) was dissolved in tetrahydrofuran (8 mL). Manganese dioxide (530 mg, 6.10=mmol) was added and the reaction mixture was stirred at room temperature for 8 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed thoroughly with ethyl acetate. The organic filtrate was concentrated to a tan solid. Drying under vacuum at 40° C. produced 3-furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (78 mg, 60%): mp 232-236° C. dec.; 1H NMR (500 MHz, CD3OD) δ 7.00-7.01 (1H, m), 7.42 (1H, s), 7.71-7.77 (2H, m), 8.16 (1H, d, J=5.6 Hz), 8.53 (1H, d, J=0.8 Hz), 8.85 (1H, s); ESI MS m/z=213 [C12H8N2O2+H]+; HPLC (Method A) >99% (AUC), tR=13.8 min.

Provenance & Evidence