tert-Butyl (3-iodophenyl)carbamate → {3-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-carbamic acid tert-butyl ester
Reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]2[NH:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[N:11]=2)=[CH:4][CH:3]=1.[C:22]([O:26][C:27](=[O:36])[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](I)[CH:30]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([O:26][C:27](=[O:36])[NH:28][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([N:8]2[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[N:11]=[C:7]2[CH2:6][C:5]2[CH:20]=[CH:21][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:34]=1)([CH3:25])([CH3:23])[CH3:24]Participants
3
Procedure
2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-1H-imidazole (1 g, 2.6 mmol) was treated with (3-iodo-phenyl)-carbamic acid tert-butyl ester following general procedure R to provide {3-[2-(4-bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-carbamic acid tert-butyl ester. The bromophenyl product (370 mg, 0.64 mmol) was treated as described in general procedure G using 4-ethoxycarbonylphenyl boronic acid to provide 4′-[1-(3-tert-butoxycarbonylamino-phenyl)-4-(2,4-dichloro-phenyl)-1H-imidazol-2-ylmethyl]-biphenyl-4-carboxylic acid ethyl ester.
Sources & evidence
- ORD record
- ord-6388258f4ce44957b9c031446627bef0
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404731B2
Reaction notes
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