[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH2:20][C:19](=[O:22])[N:18]([CH3:23])[C:17]=2[CH:24]=1)=[O:12].[H-].[Na+].[CH3:27]I>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:27])[C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH2:20][C:19](=[O:22])[N:18]([CH3:23])[C:17]=2[CH:24]=1)=[O:12]To a solution of 6-[2-(2-chloro-5-methoxy-phenyl)-acetyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (1.57 g) in tetrahydrofuran (50 ml) was added sodium hydride (55% dispersion in mineral oil, 208 mg). The mixture was stirred at room temperature for 3.5 h and then placed in an ice bath. A solution of methyl iodide (0.677 g) in tetrahydrofuran (1 ml) was added dropwise. The ice bath was removed and the mixture was stirred at room temperature for 1.5 h. The solvent was evaporated and the residue was dissolved in EtOAc. The organic phase was washed with water, dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>1:1) to give the title compound (1.09 g) as a colorless gum. MS (m/e)=360.0 [M+H+].
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