Cesium carbonate → tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

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A mixture of 6-(1H-pyrazol-4-yl)isoquinoline (130 mg, 0.67 mmol), (S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate (327 mg, 0.87 mmol) (prepared as shown in Scheme 15), and cesium carbonate (434 mg, 1.33 mmol) in DMF (5 mL) was stirred at room temperature for 24 hours. The mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (acetone/hexanes=0-40%) to provide the product as a tan solid (324 mg, 100%). LCMS (API-ES) m/z: 477 (M+H+).

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