Sodium hydride → {(2-Bromo-4-cyano-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester

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Reaction Steps

3-(3-Trifluoromethyl-phenylamino)-cyclohex-2-enone (INTERMEDIATE 3, 10.7 g, 42 mmol) is suspended in 2-methyl-tetrahydrofurane (150 mL) and sodium hydride (60% in mineral oil) (1.76 g, 43.9 mmol) is added in portions. The mixture is stirred at room temperature for 20 min and [benzenesulfonyl-(2-bromo-4-cyano-phenyl)-methyl]-carbamic acid tert-butyl ester (INTERMEDIATE 19, 16.5 g, 36.6 mmol) is added. The mixture is stirred for 1 h at room temperature. The organic phase is washed with water, dried over MgSO4 and concentrated. The product is precipitated from cyclohexane. Yield: 20.6 g. ESI mass spectrum: [M+H]+=564 (bromine isotope pattern); Retention time HPLC: 0.81 min (X012_S02).

Provenance & Evidence