[F:1][C:2]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([F:26])[C:3]=1[NH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:13]=1)[C:9]#[N:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].O>CN(C=O)C>[C:9]([C:8]1[CH:7]=[C:6]([CH2:5][NH:4][C:3]2[C:2]([F:1])=[C:24]([CH:23]=[CH:22][C:21]=2[F:26])[O:25][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:11]=1)#[N:10]To a solution of 3-[(2,6-Difluoro-3-hydroxy-anilino)methyl]-5-(3-fluorophenyl)benzonitrile (280 mg, 0.8 mmol, 1 eq) in DMF (10 mL) was added K2CO3 (550 mg, 4 mmol, 5 eq). The solution was stirred at room temperature for 30 min, then ethyl bromoacetate (200 mg, 1.2 mmol, 1.5 eq) was added dropwise. The reaction was stirred overnight, then water was added and the aqueous phase extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 15:1) to give the title compound as colorless oil (300 mg, 86%).
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