(1,3-Oxazol-2-yl)zinc chloride (0.33M in THF, 9.3 mL, 3.06 mmol) was added to a solution of N-(6-chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide (Preparation 8, 280 mg, 1.02 mmol) in THF (2 mL) and the mixture was degassed Pd(PPh3)4 (118 mg, 0.102 mmol, 10 mol %) was added and degassing was repeated. The reaction mixture was heated to 90° C. in a sealed tube and stirred overnight. The mixture was cooled and more (1,3-oxazol-2-yl)zinc chloride (0.33M, 5.0 mL, 1.65 mmol) and Pd(PPh3)4 (90 mg, 8 mol %) were added and the mixture was degassed and heated to 90° C. overnight. The reaction mixture was cooled and concentrated. The residue was purified by flash silica gel chromatography (dichloromethane/methanol 98:2) to give the title compound (80 mg, 26%) as a pale yellow solid.
