[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][N:14]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[Cl:12][C:13]1[N:14]=[CH:15][C:16]([C:17]2[NH:11][C:10]3[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=3[N:1]=2)=[CH:19][CH:20]=12,3-Diaminobenzoic acid (1; 200 mg, 1.31 mmol), 6-chloronicotinaldehyde (5; 186 mg, 1.31 mmol), and Na2S2O5 (324 mg, 1.7 mmol) were taken up in DMF (10 mL) and stirred at 100° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with H2O. The resulting mixture was stirred for 1 h at room temperature and filtered. The collected solids were washed with water, MeOH, and dried to afford 2-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid 6 as a pale solid (340 mg, yield: 95%).
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