C(Cl)Cl.[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[CH:27]=[C:26]([CH2:28][NH:29][CH3:30])[CH:25]=[CH:24][C:14]=2[O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=[C:10]([F:12])[CH:11]=1)#[N:5].CCN(CC)CC.[F:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>O>[C:4]([C:6]1[CH:7]=[C:8]([C:13]2[CH:27]=[C:26]([CH2:28][N:29]([CH3:30])[S:45]([C:42]3[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=3)(=[O:47])=[O:46])[CH:25]=[CH:24][C:14]=2[O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=[C:10]([F:12])[CH:11]=1)#[N:5]To an anhydrous DCM (50 mL) solution of t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate (22) (28 g, 72 mmol), was added Et3N (8.6 g, 85 mmol) followed by portionwise addition of 4-fluoro-benzenesulfonyl chloride (16.6 g, 85 mmol). The mixture was stirred at room temperature for 20 min and water (20 mL) was added. The organic layer was separated, dried and concentrated in vacuo. The crude was purified by column chromatography to give t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (23) (24 g, 63%).
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