[F:1][C:2]1[C:8](F)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]N)=[CH:16][CH:15]=1.CS(C)=O.CCN(CC)CC>O.II>[F:1][C:2]1[C:8]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4]
A round bottom flask was charged with 2,3-difluoro-6-nitroaniline (0.50 g, 2.87 mmol, 1.00 equiv.) and 4-bromobenzylamine (0.959 g, 5.15 mmol, 1.80 equiv.). Dimethyl sulfoxide (2.5 mL) was then added flowed by Et3N (0.968 mL, 6.88 mmol, 2.40 equiv.) and I2 (catalytic, 10 mg). The reaction mixture was heated to 120° C. and stirred for 3 h. The reaction mixture was then cooled to ambient temperature, diluted with water (75 mL) and extracted with Ethyl acetate (2×60 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give crude material, which was purified by silica gel column chromatography (10% ethyl acetate/hexane) to afford compound 3 as the desired product (0.869 g, 89%).
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