[7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol → [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone

Participants

Reaction Steps

A mixture of [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanol (Example 46) (1.13 g, 2.69 mmol) and MnO2 (2.35 g, 27.0 mmol) in methylene chloride (75 mL) was stirred under a nitrogen atmosphere at room temperature overnight (17 h). The crude reaction mixture was filtered through diatomaceous earth, rinsing with methylene chloride. The filtrate was concentrated to give a dark oil. Purification by Biotage chromatography (10-30% ethyl acetate in hexanes) provided [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone as a yellow solid: mp 122-124° C.; 1H NMR (300 MHz, CD3OD) δ4.76 (4H, s), 5.49 (1H, s), 6.25 (1H, s), 7.11 (1H, s) 7.15-7.30 (10H, m), 7.56-7.72 (4H, m), 7.94-7.97 (2H, m); ESI MS m/z 418 [C28H23N3O+H]+; HPLC (Method A) >99% (AUC), tR=20.2 min.

Provenance & Evidence