Potassium Phosphate, Tribasic → HCID 86703751, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-chloro-4-((2,6-dimethylcyclohexyl)-methoxy)-2-fluorobenzoate (0.43 g, 1.16 mmol), cyclopropylboronic acid (0.14 g, 1.74 mmol), potassium phosphate (1.48 g, 7.00 mmol) and tricyclohexylphosphine tetrafluoroborate (0.085 g, 0.230 mmol) in toluene (5 mL) and water (0.5 mL) under a nitrogen atmosphere was added palladium acetate (0.04 g, 0.12 mmol). The reaction mixture was heated at 130° C. for 30 minutes in the microwave then cooled to ambient temperature. Water (20 mL) was added and the mixture extracted with ethyl acetate (3×10 mL), the combined organics were washed with brine; dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography (5% ethyl acetate in hexanes) afforded tert-butyl 5-cyclopropyl-4-((2,6-dimethylcyclohexyl)methoxy)-2-fluorobenzoate (0.43 g, 1.16 mmol) which was used directly into the next step. To a solution of this compound (0.43 g, 1.16 mmol) in dichloromethane (2 mL), was added trifluoroacetic acid (2 mL). The reaction mixture was stirred at 0° C. for 1 hour and then concentrated in vacuo. The residue was purified by column chromatography (0 to 30% ethyl acetate in hexanes) to afford the title compound (0.142 g, 38%). MS (ES−) m/z 319.2 (M−1).

Provenance & Evidence