Tetrabutylammonium Fluoride → Benzamide

Participants

Reaction Steps

A solution of 4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-N-tert-butyl-benzamide (300 mg, 0.57 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 5 mL, 5 mmol) was stirred at room temperature for 12 h. The mixture was diluted with ethyl acetate (150 mL), washed with a saturated aqueous ammonium chloride solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-tert-butyl-4-[2-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-benzamide (220 mg, quant.) as a white solid: LC/MS m/e calcd for C25H29N3O [M+H]+ 388.53, observed 388.2.

Provenance & Evidence