Potassium Carbonate → HCID 58042459, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed suspension of tert-butyl 4-bromobenzoate (Preparation 257, 250 mg, 0.97 mmol), 5-chloro-6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)pyridin-3-amine (Preparation 256, 430 mg, 1.46 mmol) and potassium carbonate (403 mg, 2.92 mmol) in a mixture of terbutanol (10 ml)/water (0.2 ml) was added Pd(OAc)2 (1 mol %) and BrettPhos (3 mol %). The mixture was heated at 110° C. for 18 hours. After 18 hours, further portions of Pd(OAc)2 (1 mol %) and BrettPhos (3 mol %) were added and the reaction was heated for 24 hours at 110° C. The reaction was cooled to room temperature, ethyl acetate (50 mL) and water (15 mL) were added, the phases were separated and the combined organics evaporated. The crude product was purified by silica gel column chromatography, eluting with DCM in Heptane (10% to 80%), to give the title compound as an oil (0.22 g, 48%).

Provenance & Evidence