Potassium Phosphate, Tribasic → tert-Butyl 4-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(3-(5-bromopyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (Example 33, step 4) (1.64 g, 3.68 mmol) in toluene (12 mL) and water (0.6 mL) under a N2 atmosphere was added cyclopropyl boronic acid (410 mg, 4.77 mmol), potassium phosphate (2.24 g, 12.9 mmol), tricyclohexyl phosphine (103 mg, 0.367 mmol) and palladium acetate (41.2 mg, 0.184 mmol). The mixture was heated at 80° C. overnight. The reaction was cooled to RT and water was added. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-50% EtOAc/hexane) gave the title compound as an oil that solidified on the vacuum pump (1.3 g, 87% yield).

Provenance & Evidence