[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:6][C:5]=1N.N([O-])=O.[Na+].[IH:24].C(=O)(O)[O-].[Na+]>CS(C)=O>[I:24][C:5]1[CH:6]=[C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:19])([F:18])[F:1]To a solution of 2-trifluoromethoxy-5-(4-methyl-piperazin-1-yl)-phenylamine (5.0 g, 0.018 mol), sodium nitrite (5.1 g, 0.0734 mol) in dimethyl sulfoxide (180 mL) a solution of 57% hydroiodic acid (9.6. mL, 0.0427 mol) in dimethyl sulfoxide were added dropwise at room temperature in 20 minutes. The reaction was stirred for 5 hours at 35° C., then cooled in a ice bath and sodium bicarbonate in small portion was added until basic pH. The aqueous layer was extracted with dichoromethane (3×500 mL), the organic phases washed with 10% solution of sodium bisulphite (2×500 mL) then water (1×300 mL). The organic phase was dried over anhydrous Na2SO4, the solvent evaporated under vacuum to yield the intermediate (2.4 g, 34%) as a orange solid which was used as such in the next step.
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