Ethyl cyanoformate → 4-Benzyl 2-ethyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2,4-dicarboxylate
Reaction equation
Br[C:2]1[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:6]=1.C([C:27]([O:29][CH2:30][CH3:31])=[O:28])#N>>[CH3:22][Si:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][O:18][CH2:17][N:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:6]=[C:2]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]Participants
3
Procedure
The title compound was prepared using the procedure described in Example 52(d) starting from benzyl 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (0.609 mmol, 250 mg) and ethyl cyanoformate (0.91 mmol, 90 mg). Yield 97 mg. 1H-NMR (400 MHz; CDCl3): δ −0.08 (s, 9H), 0.91 (t, 2H), 1.42 (t, 3H), 3.57 (t, 2H), 4.43 (q, 2H), 5.38 (s, 2H), 5.78 (s, 2H), 7.30-7.39 (m, 3H), 7.43-7.46 (m, 2H), 7.90 (s, 1H). LC-MS: [M+1]=405.13.
Sources & evidence
- ORD record
- ord-260cb27c67d9457d8cc936be65c28888
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921378B2
Reaction notes
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