[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl.Cl[CH2:13][C:14]1[N:15]([CH2:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[CH:16]=[CH:17][N:18]=1>CN(C=O)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[C:24]([Cl:26])[CH:23]=1)[CH2:19][N:15]1[CH:16]=[CH:17][N:18]=[C:14]1[CH2:13][O:8][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=13-Aminophenol (87 mg, 0.8 mmol) was dissolved in DMF and NaH (33 mg, 0.83 mmol) was added. After 10 min, 2-(chloromethyl)-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) (100 mg, 0.32 mmol) was added in one portion. After 20 min, the reaction was partitioned between water (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous layer was re-extracted with EtOAc (1×10 mL). The combined organic layers were washed with 1M NaOH (3×10 mL), water (10 mL) and brine, dried over MgSO4, filtered and concentrated to yield the title compound as a pale yellow oil (78 mg, 70%); MS m/z 348 [C17H15Cl2N3O+H]+.
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