[N+:1]([C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.O.NN>CCO.O.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=3)[NH:10][C:7]2=[N:8][CH:9]=1To a stirred suspension of 6-Nitro-2-(4-nitrophenyl)-3H-imidazo [4,5-b]pyridine (4) (0.5 g, 1.75 mmol) in EtOH (40 mL) was added Raney Ni° (1 g, slurry in H2O) followed by hydrazine hydrate (2 mL) dropwise over 5 minutes. The reaction mixture was stirred at room temperature until the reaction subsided and was then heated at 100° C. for 1 h. The hot solution was filtered through celite and the filtrate concentrated under reduced pressure. Water was added to the residue resulting in the formation of an off white solid that was collected by filtration, rinsed with H2O and air dried. The solid was then dried in vacuuo at room temperature to give 5 as a light tan solid (0.318 g, 1.4 mmol, 81%) 1H NMR (500 MHz, DMSO-d6) δ12.27 (apparent d, 1H), 7.77 (br s, 2H), 7.70 (br s, 1H) 6.97 (br s, 1H), 6.63 (d, J=8.51 Hz, 2H), 5.57 (br s, 2H), 4.97 (br s, 2H)
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