Potassium Phosphate, Tribasic → HCID 86703530, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-chloro-2-fluoro-4-((1-(trifluoromethyl)cyclobutyl)-methoxy)benzoate (2.11 g, 5.5 mmol), cyclopropylboronic acid (0.94 g, 11.0 mmol), potassium phosphate (5.25 g, 24.8 mmol) and tricyclohexylphosphine tetrafluoroborate (0.4 g, 1.10 mmol) in toluene (60 mL) and water (3 mL) under a nitrogen atmosphere was added palladium acetate (0.25 g, 1.10 mmol). The reaction mixture was heated to 110° C. for 18 hours and then cooled to ambient temperature. Water (20 mL) was added and the mixture extracted with ethyl acetate, the combined organics were washed with brine; dried over anhydrous sodium sulfate and concentrated in vacuo., the crude product tert-butyl 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)cyclobutyl)-methoxy)benzoate was dissolved in dichloromethane (30 mL) and added trifluoroacetic acid (10 ml). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated in vacuo. The residue was purified by column chromatography (5% to 60% ethyl acetate contains 0.2% acetic acid in hexanes) afforded the title compound was obtained as colorless solid (0.50, 27%): MS (ES+) m/z 333.1 (M+1); MS (ES−) m/z 331.2 (M−1).

Provenance & Evidence