[NH2:1][C:2]1[C:3]([NH:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[C:18](O)(=O)C.C(N)=N>C(O)C>[Cl:8][C:5]1[N:4]=[C:3]2[N:9]([C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=3)[C:13]#[N:14])[CH:18]=[N:1][C:2]2=[CH:7][CH:6]=1In step 1-3, a solution of 3-(3-amino-6-chloropyridin-2-ylamino)benzonitrile (1.07 g, 4.38 mmol) and foramidine acetate (1.37 g, 13.1 mmol) in ethanol was refluxed for 3 hours. The reaction mixture was concentrated and purified to afford 3-(5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)benzonitrile (1-3) as a yellow solid.
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