Water → HCID 69673293, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added tert-butyl 4-(3-bromo-5-fluorophenoxy)piperidine-1-carboxylate (215 mg, 0.574 mmol), cesium carbonate (562 mg, 1.72 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (130 mg, 0.27 mmol), potassium [(dimethylamino)methyl](trifluoro)borate(1-) (114 mg, 0.689 mmol), palladium acetate (30.7 mg, 0.137 mmol) and 5.05M water in THF (3.5 mL). The tube was sealed and evacuated and refilled with N2 (3×). The sealed tube was then heated at 80° C. for 20 hours. The reaction was diluted with water and ethyl acetate. The aqueous layer was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified with preparative LCMS (C18 column eluting with a gradient of ACN/H2O containing 0.1% TFA) to afford the desired product (180 mg, 89%). LCMS (M+H)+: 353.2.

Provenance & Evidence