Potassium Phosphate, Tribasic → HCID 86703557, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-chloro-2-fluoro-4-((8-methyl-1,4-dioxaspiro[4.5]decan-8-yl)methoxy)benzoate (3.09 g, 7.45 mmol), cyclopropylboronic acid (0.96 g, 11.17 mmol), potassium phosphate (7.12 g, 33.53 mmol) and tricyclohexylphosphine tetrafluoroborate (0.28 g, 0.75 mmol) in toluene (50 mL) and water (2.5 mL). The resulting suspension was sparged with Argon for 15 minutes before the addition of palladium acetate (0.083 g, 0.37 mmol). The reaction mixture was heated at 100° C. for 18 hours and then cooled to ambient temperature; filtered through a pad of diatomaceous earth and rinsed with ethyl acetate. The filtrate was diluted with additional water (20 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was filtered through a plug of silica gel (100% ethyl acetate) to afford the title compound (2.59 g, 83%) as a colorless oil: MS (ES+) m/z 365.2 (M−55).

Provenance & Evidence