Ethyl Acetate → HCID 59451442, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-Bromo-6-(methyloxy)-1H-indole-2-carboxylate (0.075 g, 0.26 mmol) was dissolved in CH2Cl2 (5 mL), cooled to 0° C. under nitrogen and BBr3 (1.0 M in CH2Cl2, 1.6 mL, 1.6 mmol) added dropwise. The reaction mixture was allowed to warm to RT and stirred overnight. Ice cold water (1 mL) and EtOAc (5 mL) were added. The layers were separated and the aqueous layer extracted with EtOAc (3×5 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.005 g, 7%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 13.06 (br. s., 1H), 11.63 (br. s., 1H), 9.55 (s, 1H), 7.30 (d, 1H), 6.78 (d, 1H), 6.70 (dd, 1H). MS: m/z 256.13 (M+1).

Provenance & Evidence