Potassium Hydroxide → HCID 58056555, compound

Participants

Reaction Steps

Into a flask, 3-(5-fluoro-1H-indol-3-yl)-propionic acid methyl ester (3, 530.000 mg, 2.39572E-3 mol), 3-bromo-2-methyl-benzene sulfonyl chloride (4, 710.33 mg, 0.0026353 mol), 62.35 mL methylene chloride, 17 mL 50% KOH and a catalytic amount of tetra-n-butyl ammonium hydrogen sulfate were combined and stirred at room temperature for 48 hours. The organic layer was washed with saturated sodium bicarbonate, dried over MgSO4 and filtered. The organic layer was concentrated at reduced pressure to afford a tannish solid. Purification by flash chromatography using a gradient of 0-25% ethyl acetate in hexanes over 35 minutes yielded the desired compound (5, 650 mg, 59.72%). 1H NMR consistent with desired compound. MS(ESI) [M+H+]+==454.0, 456.0.

Provenance & Evidence