Triethylamine → (E)-[2-(3-{4-[(2-Morpholin-4-yl-ethoxy)-(4-trifluoromethyl-phenylcarbamoyl)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

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A mixture of 2-(4-bromo-phenyl)-2-(2-morpholin-4-yl-ethoxy)-N-(4-trifluoromethyl-phenyl)-acetamide (481 mg, 0.720 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (240 mg, 0.920 mmol), tri-o-tolyl-phosphine (51 mg, 0.17 mmol), triethylamine (421 mg, 4.16 mmol) and Pd2(dba)3 (76 mg, 0.08 mmol) in DMF (4 mL) was heated at 105 degrees Celcius for 1 hr under N2 atmosphere, and then at 95 degrees Celcius overnight. After cooling to room temperature, the mixture was poured into a saturated aqueous solution of NH4Cl and extracted with ethyl acetate four times. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography (dichloromethane/methanol 500:1-100:1) to obtain a brown solid (118 mg, 24.6%). MS: calc'd 669 (MH+), exp 669 (MH+).

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