N-bromobutanimide → HCID 86610212, compound

Participants

Reaction Steps

1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carboxylic acid thiazol-2-ylamide (2.5 mmol), N-bromosuccinimide (6 mmol) was stirred in HOAc (25 mL) over night at room temperature. The reaction mixture was evaporated to dryness and the crude product was purified by flash chromatography (Horizon, EtOAc-heptane) to give 1-cyclopropylmethyl-6-fluoro-1H-indole-3-carboxylic acid (5-bromo-thiazol-2-yl)-amide in 32% yield. A solution of 1-cyclopropylmethyl-6-fluoro-1H-indole-3-carboxylic acid (5-bromo-thiazol-2-yl)-amide (0.2 mmol), p-cresol (0.2 mmol) and potassium-t-butoxide (0.44 mmol) in DME (3 mL) was heated in a closed vessel in a Smith Creator microwave oven for 300 s at 120° C. Addition of water followed by extraction with DCM, drying of the organic phase followed by purification by preparative HPLC (Method E) gave the title compound.

Provenance & Evidence