[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1.Br[C:16]1[CH:17]=[CH:18][C:19]([Cl:23])=[C:20]([CH3:22])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([C:16]3[CH:17]=[CH:18][C:19]([Cl:23])=[C:20]([CH3:22])[CH:21]=3)[C:7](=[O:12])[C:8]([CH3:10])([CH3:11])[O:9][C:4]=2[CH:3]=1A mixture of 7-amino-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 3(1); 150 mg), 5-bromo-2-chlorotoluene (321 mg), copper(I) iodide (37 mg), potassium carbonate (216 mg), N,N′-dimethylethylenediamine (40 μL) and toluene (8 mL) was heated at 110° C. overnight under argon atmosphere. After cooling, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=4/1→1/1) to give 7-amino-4-(4-chloro-3-methylphenyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one (98 mg) as a pale orange powder.
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