Sodium hydride → 1-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)-3,3-diphenylpyrrolidin-2-one

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Reaction Steps

To a solution of 3,3-diphenylpyrrolidin-2-one (Example 1A) (0.062 g, 0.262 mmol) in N,N-dimethylformamide (2 mL) was added 60% sodium hydride dispersion in oil (0.013 g, 0.314 mmol). The mixture was stirred at room temperature for 1 hour. Then a solution of 5-(bromomethyl)-4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole (CAS 439134-78-8) (0.088 g, 0.262 mmol) in N,N-dimethylformamide (1 mL) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was partitioned between H2O and dichloromethane. The organic layer was separated, dried over MgSO4 and concentrated. The obtained residue was purified by silica gel chromatography eluting with 2-5% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.95-8.00 (m, 2H), 7.65-7.70 (m, 2H), 7.17-7.37 (m, 10H), 4.72 (s, 2H), 3.35 (t, J=6.4 Hz, 2H), 2.76 (t, J=6.3 Hz, 2H), 2.47 (s, 3H); MS (ESI+) m/z 493 (M+H)+.

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