C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([F:19])[CH:18]=1)[NH2:15].Cl[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22]>C1COCC1.CCOCC>[F:11][C:12]1[CH:13]=[C:14]([NH:15][C:21](=[O:22])[O:23][CH:24]([CH3:26])[CH3:25])[CH:16]=[C:17]([F:19])[CH:18]=1Lithium bis(trimethylsilyl) amide (1.0 M solution in tetrahydrofuran, 542 mL, 0.542 mol) was added to a solution of 3,5-difluoroaniline (35 g, 0.271 mol) in THF (60 mL) at 0° C. Isopropyl chloroformate (1M solution in toluene, 406 mL, 0.406 mol) was then added dropwise at 0° C. and the mixture allowed to warm to room temperature over 2 h. The reaction mixture was diluted with ether and washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, brine and dried (MgSO4). Solvent was removed under vacuum and the residue was triturated in hexanes to obtain the title compound.
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