[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH4+].[Cl-].O>[Fe].CO>[S:11]1[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=[C:10]1[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1A mixture of 2-(3-nitrophenyl)thiazolo[4,5-c]pyridine (1.53 g, 5.9 mmol), NH4Cl (2.76 g, 51.6 mmol), iron powder (1.80 g, 32.2 mmol), H2O (30 mL) and methanol (120 mL) was heated to reflux for 5.5 h under N2. The mixture was filtered and the filtrate was diluted with H2O (400 mL). The precipitate was collected by filtration and dried in vacuo to afford 3-(thiazolo[4,5-c]pyridin-2-yl)benzenamine as a brown solid (841 mg, 63%). 1HNMR (400 MHz, DMSO-d6) δ: 9.28 (1H, s); 8.52 (1H, s); 8.21 (1H, s); 7.23-7.38 (3H, d), 6.79 (1H, s), 5.51 (2H, s); MS (ESI) calcd. for C12H9N3S (m/z): 227. found: 228 [M+H]P
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