[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:21]I.Cl>C1COCC1.O>[F:3][C:4]1[CH:5]=[C:6]([N:10]([CH3:21])[C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1
NaH 60% dispersed in mineral oil (0.024 g; 0.611 mmol) was added to a solution of methyl 4-(3-fluorophenylamino)benzoate in THF (3 mL). After stirring the resulting solution for 10 minutes methyl iodide (0.062 mL; 0.994 mmol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with water, acidified with a 6N solution of hydrochloride acid and extracted with ethyl acetate. The organic layer was dried to yield 0.119 g (quantitative) of the title compound as a brown solid. The compound was used without further purification.
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