[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[I:28]I.[OH-].[K+].OS([O-])=O.[Na+]>O1CCCC1.O.N1C=CC=CC=1>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([I:28])=[CH:4][N:3]=1
A solution of 1-(4-(4-aminothieno[3,2-c]pyridin-3-yl)phenyl)-3-(3-fluorophenyl)urea (example 49 in WO2005/10009) (12.2 g, 32.2 mmol) and pyridine (75 mL) in tetrahydrofuran (250 mL) was treated with iodine (36.8 g, 145 mmol) at room temperature. The reaction mixture was heated to 50° C. for 3.5 hours, then cooled to room temperature and treated with 20% aqueous KOH (18.1 g) followed by a 10% aqueous NaHSO3 solution (134 g) added in portions. The resulting mixture was heated to 60° C., diluted with water (366 mL), cooled to room temperature, and filtered. The wet cake was dried to provide the title compound.
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