Sodium Carbonate → tert-Butyl 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate (Example 71, Step 2) (91 mg, 0.18 mmol) in anhydrous toluene (3 mL) and ethanol (3 mL) was added phenyl boronic acid (43.7 mg, 0.358 mmol) and 2M Na2CO3 (0.53 mL, 1.08 mmol). This solution was degassed for 20 min and Pd(PPh3)4 (19 mg, 10 mol %) was added. The reaction was heated at 90° C. overnight. The reaction was cooled and extracted with EtOAc (3×). The organic layer was dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) gave the title compound as a foam (60 mg, 66% yield).

Provenance & Evidence