Stannane, tributyl(1-ethoxyethenyl)- → Methyl 2-(1-ethoxyvinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].C([Sn](CCCC)(CCCC)[C:24]([O:26][CH2:27][CH3:28])=[CH2:25])CCC>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:27]([O:26][C:24]([C:7]1[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]=1)=[CH2:25])[CH3:28]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
Methyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (10 g, 29.9 mmol) was dissolved in dioxane (200 ml). Tributyl(1-ethoxy-vinyl)stannane (16.2 g, 44.8 mmol) was added to the solution. The resulting mixture was degassed and purged with argon for 20 min. Then Pd(PPh3)4 (3.45 g, 2.99 mmol) was added and the mixture was refluxed overnight. The reaction mixture was cooled to RT and diluted with cold water. The mixture was extracted with EtOAc and washed with aqueous KF solution. The organic layer was concentrated to give the desired product. Yield 12.1 g. LC-MS: [M+1]=327.78.
Workup
- customThe resulting mixture was degassed
- custompurged with argon for 20 min
- temperaturethe mixture was refluxed overnight
- extractionThe mixture was extracted with EtOAc
- washwashed with aqueous KF solution
- concentrationThe organic layer was concentrated
Sources & evidence
- ORD record
- ord-30a2ec426d9c4cd7af05a8609c857d29
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921378B2
Reaction notes
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