Potassium Phosphate, Tribasic → HCID 86703534, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-chloro-4-((4,4-difluoroadamantan-1-yl)methoxy)-2-fluorobenzoate (1.50 g, 3.48 mmol), cyclopropylboronic acid (0.45 g, 5.22 mmol), potassium phosphate (3.33 g, 15.7 mmol) and tricyclohexylphosphine tetrafluoroborate (0.13 g, 0.35 mmol) in toluene (60 mL) and water (3 mL) under a nitrogen atmosphere was added palladium acetate (0.08 g, 0.35 mmol). The reaction mixture was heated to 100° C. for 18 hours and then cooled to ambient temperature. Water (20 mL) was added and the mixture was filtered through a pad of diatomaceous earth and the solid was washed with ethyl acetate (150 mL). The organics were washed with brine; dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by crystallization (ethyl acetate and hexanes) afforded the title compound as colorless solid (1.00 g, 66%): 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=8.4 Hz, 1H), 6.47 (d, J=12.6 Hz, 1H), 3.57 (s, 2H), 2.29 (br s, 2H), 2.02-1.95 (m, 6H), 1.75-1.68 (m, 6H), 1.57 (s, 9H), 0.93-0.87 (m, 2H), 0.65-0.60 (m, 2H); MS (ES+) m/z 459.2 (M+23).

Provenance & Evidence