Water → HCID 59762957, compound

Participants

Reaction Steps

Alluminium trichloride (0.550 g, 2.50 mmol, 2.2 eq) was added to a solution of benzoyl chloride (0.319 g, 2.274 mol, 2 eq) in anhydrous DCM (5 ml). After stirring at room temperature under Ar for 30 min, methyl 5-carboxy indole (0.199 g, 1.157 mmol) was added. After stirring for 2 h at room temperature, the reaction mixture was poured into water (5 ml). The product was extracted with DCM (3×10 ml). The organic extracts were collected, dried over Na2SO4 and the solvent removed under reduced pressure to afford a brown solid. The pure compound rpm123 was obtained after trituration with hexane (10 ml) as a off-whte solid (0.205 g, 0.737 mmol, 64%), mp 271-273° C. 1H (400 MHz, DMSO-d6) δ 3.87 (3H, s), 7.52-7.61 (4H, m), 7.79-7.31 (2H, m), 7.87 (1H, dd, J 1.4, 8.6 Hz), 8.08 (1H, d, J 3.2 Hz), 8.9 (1H, d, J 1.2 Hz), 12.36 (1H, s). 13C NMR (100 MHz, DMSO-d6) δ 190.64, 167.70, 140.74, 140.16, 138.34, 132.07, 129.19, 129.14, 126.61, 124.77, 124.51, 123.93, 116.30, 113.13, 52.61.

Provenance & Evidence