Tetrabutylammonium Fluoride → HCID 10359151, compound

Participants

Reaction Steps

To a solution of 55 mg (0.100 mmol) [2-({5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzo[b]thiophene-2-carbonyl}-amino)-phenyl]-carbamic acid tert-butyl ester (40) in 5 ml tetrahydrofurane was added 38 mg (0.120 mmol) tetra-n-butylammonium fluoride. The reaction mixture was stirred at room temperature for 1 h and poured into brine. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed brine and dried over sodium sulfate. The solvent was evaporated and the residue of (2-{[5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester was dissolved in 1.0 ml trifluoroacetic acid. The reaction mixture was stirred for 45 min at room temperature and then added to an aqueous solution of sodium bicarbonate. After extraction with ethyl acetate and removal of the solvent the residue was recrystallized from ethyl acetate/diethyl ether to yield 17 mg (0.052 mmol) of 5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carboxylic acid (2-amino-phenyl)-amide (39) as a white solid, mp. 215–216° C.

Provenance & Evidence