F[C:2]1[C:12]([F:13])=[CH:11][C:10]([I:14])=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[NH2:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[F:13][C:12]1[C:2]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:3]([CH:9]=[C:10]([I:14])[CH:11]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]2,3-Difluoro-5-iodo-N,N-dimethyl-benzamide (507, 1.63 mmol), 4-(aminomethyl)-pyridine (1.8 ml, 17.73 mmol), di-iso-propylethylamine (0.31 ml, 1.78 mmol), and dioxane (3 ml) were combined and stirred for 18 hours at 75° C. The reaction mixture was concentrated in vacuo to give approximately 650 mg of crude 3-fluoro-5-iodo-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide, which was used directly in the next step. MS: m/z 400.2 (M+H+).
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