Tetrabutylammonium Fluoride → 3-{4-[2-(4-Chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Dissolve 3-(4-{[5-(4-chloro-phenyl)-3-trimethylsilanylethynyl-thiophene-2-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (420 mg, 0.69 mmol) in THF (11 mL) and add 1 M tetrabutylammonium fluoride (1.50 mL, 1.50 mmol, solution in THF). Stir the solution at RT overnight. Dilute the solution with EtOAc (100 mL) and wash with water (3×50 mL) and brine (50 mL). Dry the organic solution, filter, and concentrate the filtrate. Purify the crude material by flash chromatography, using a linear gradiant of 30-70% EtOAc/hexanes, to give 280 mg (75%) of the title compound. LC-MS/ES m/z (35Cl) 483.0 [M−t-butyl+H]+.

Provenance & Evidence