Ammonium formate → HCID 57893551, compound

Participants

Reaction Steps

A mixture of [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone (Example 55) (674 mg, 1.61 mmol), ammonium formate (2.04 g, 32.3 mmol) and 10% palladium on carbon (350 mg, 50% by wt.) in methanol (40.2 mL) and ethanol (40.2 mL) was heated under reflux for 1 h. The reaction mixture was filtered through diatomaceous earth to remove the catalyst. After concentration to dryness, the residue was treated with a small amount of methanol (ca. 3 mL) and a precipitate formed. The solid was filtered, rinsed with a small amount of methanol, and collected. Additional material was obtained from Biotage chromatography of the filtrate. This provided (5-amino-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (119 mg, 32%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ5.81 (1H, s), 5.94 (1H, s), 6.44 (1H, s), 7.27-7.53 (5H, m), 8.06 (1H, s), 8.20 (1H, s), 10.9 (1H, br s); ESI MS m/z 240 [C14H13N3O+H]+; HPLC (Method A) 89.0% (AUC), tR=14.0 min.

Provenance & Evidence