HCID 57893459, compound → HCID 57893472, compound

Participants

Reaction Steps

(5-Chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (Example 140) (105 mg, 0.41 mmol) was dissolved in methylene chloride (10 mL). Manganese dioxide (358 mg, 4.1 mmol) was added and the reaction mixture was stirred for 60 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with methylene chloride. The filtered was concentrated to give a pink solid. Recrystallization from methylene chloride gave (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanone (73 mg, 70%) as a white solid: mp 194-197° C.; 1H NMR (300 MHz, CDCl3) δ7.10 (1H, s), 7.51-7.75 (4H, m), 8.01 (2H, m), 8.79 (1H, s), 9.57 (1H, br s); ESI MS m/z 257 [C14H9ClN2O+H]+; HPLC (Method A) >99% (AUC), tR=21.5 min.

Provenance & Evidence