[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]1[NH:13][CH2:14][NH:15][CH:16]=1.C([O-])(O)=O.[Na+].C1C=CC(OC(Cl)=[S:30])=CC=1>C1COCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]1[NH:13][C:14](=[S:30])[NH:15][CH:16]=1
4-(4-Chloro-indol-1-ylmethyl)-1,3-dihydro-imidazole (Intermediate A4) (0.5 mmol) in THF (3 mL) and water (3 mL) was treated with NaHCO3 (5 mmol) at rt for 20 m. Phenyl chlorothionoformate (1.3 mmol) was added and stirring was continued for 4 h. The mixture was diluted with water (15 mL) and extracted with ether (3×25 mL). The organic portions were combined, dried over MgSO4, filtered and the solvent was removed under vacuum. The residue was dissolved in MeOH (4 mL) and treated with NEt3 (0.35 mL) for 18 h at rt. The solvent was evaporated and the product was washed on a glass frit with 50% CH2Cl2:hexanes to give a solid 4-(4-chloro-indol-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 1) (˜50%)
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