1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-2-pyridinyl- → (pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

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Reaction Steps

(Pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 117) (55 mg, 0.24 mmol) was dissolved in tetrahydrofuran (4 mL). Manganese dioxide (210 mg, 2.42 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed thoroughly with tetrahydrofuran. The organic filtrate was concentrated to a yellow solid. Drying under vacuum at 40° C. produced (pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (60 mg, quant.): mp 219-222° C.; 1H NMR (500 MHz, CD3OD) δ7.66-7.76 (2H, m), 7.85 (1H, m), 8.04-8.08 (1H, m), 8.14-8.21 (2H, m), 8.82-8.43 (1H, m), 8.92 (1H, s); ESI MS m/z=224 [C13H9N30+H]+; HPLC (Method A) 95.4% (AUC), tR=13.1 min.

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