m-Chloroperbenzoic acid → HCID 67155645, compound

Participants

Reaction Steps

1-Tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (5 g, 16.65 mmol) was dissolved in DCM (165 mL) and chilled to 0° C. m-Chloroperbenzoic acid (“m-CPBA”; 4.85 g, 21.64 mmol, 77% by weight) was added, and the mixture was allowed to gradually warm to room temperature over a 16 hour period. The mixture was then washed with 10% aqueous sodium sulfite solution, dried over sodium sulfate and concentrated. Flash 65 Biotage (5% ethyl acetate/DCM) afforded 1-tosyl-1H-pyrrolo[2,3-b]pyridin-3 (2H)-one (441 mg, 9%). 1H NMR (400 MHz, CDCl3) δ 8.61-8.66 (m, 1H), 8.00-8.05 (m, 2H), 7.92-7.97 (m, 1H), 7.29-7.34 (m, 2H), 7.06-7.12 (m, 1H), 4.38 (s, 2H), 2.41 (s, 3H).

Provenance & Evidence