2,6-Lutidine → 3-Methyl-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde

Participants

Reaction Steps

OsO4 (29 mg, 0.12 mmol) was added to a stirred mixture of 3-methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole (342 mg, 1.15 mmol; Intermediate 30) and 2,6-lutidine (268 μL, 2.3 mmol) in dioxane (15 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.984 g, 4.6 mmol) in water (5 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 50 min, combined with an earlier batch of this intermediate (followed this experimental and starting with 3-methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole, 70 mg; Intermediate 30), extracted with water (30 mL) and DCM (2×30 mL). The organic layers were combined, dried, filtered and concentrated to give the title compound (463 mg, 89%) as a black solid. MS (ESI+) for C16H13NO3S m/z 300 (M+H)+.

Provenance & Evidence