Acetic Anhydride → 1-acetyl-6-bromo-5-fluoro-2-methyl-1H-indol-3-yl acetate

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Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-((1-carboxyethyl)amino)-5-fluorobenzoic acid (D86) (1.599 g, 5.22 mmol), sodium acetate (1.714 g, 20.90 mmol) and acetic anhydride (19.72 mL, 209 mmol) was heated at 150° C. for 30 min in a microwave. The mixture was evaporated in vacuo. The residue was diluted with DCM and poured into saturated NaHCO3 aq. (200 mL). The mixture extracted with DCM (30 mL×3). The organic layers were combined, washed with brine (100 mL), filtered through phase separator and evaporated in vacuo. The crude residue was purified by chromatography on silica, eluting with a gradient of 0-35% ethyl acetate in cyclohexane to give title compound (1.233 g). LCMS (A): m/z (M+H)+ 328/330, C13H11BrFNO3 requires 327/329 (acidic).

Provenance & Evidence