Trimethyltin chloride → 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2-methyl-4-(trimethylstannyl)-1H-imidazole
Reaction equation
[Si:1]([O:8][C:9]([CH3:19])([CH3:18])[CH2:10][N:11]1[CH:15]=[C:14](I)[N:13]=[C:12]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Br)C.[CH3:24][Sn:25](Cl)([CH3:27])[CH3:26]>C(Cl)Cl>[Si:1]([O:8][C:9]([CH3:19])([CH3:18])[CH2:10][N:11]1[CH:15]=[C:14]([Sn:25]([CH3:27])([CH3:26])[CH3:24])[N:13]=[C:12]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
To a mixture of 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-iodo-2-methyl-1H-imidazole (1.5 g, 3.8 mmol) in DCM (15 mL) was added ethylmagnesium bromide (1.9 mL, 3 mol/L, 5.7 mmol) at −78° C. The temperature of the mixture was allowed to warm up to about 10° C. slowly and cooled again. Trimethyltin chloride (6.5 ml, 1 mol/L, 6.5 mmol) was added dropwise at −78° C. After the addition, the temperature was allowed to slowly warm up to room temperature. The reaction mixture was pouted into saturate NH4Cl solution, then extracted with DCM, The organic was washed with water twice, dried over anhydrous Na2SO4, concentrated to give 0.44 g of 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2-methyl-4-(trimethylstannyl)-1H-imidazole. Yield=63%. 1H NMR (CDCl3, 400 MHz): δ 7.04 (s, 1 H, ArH), 3.74 (s, 2 H), 2.43 (s, 3 H), 1.24-1.20 (m, 6 H), 0.88 (s, 9 H), 0.29 (s, 6 H), 0.03 (s, 8 H). LC-MS: m/z=375 [M+H+]
Workup
- temperaturecooled again
- additionAfter the addition
- temperatureto slowly warm up to room temperature
- concentrationinto saturate NH4Cl solution
- extractionextracted with DCM
- washThe organic was washed with water twice
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c239cb8f5b834851adfef6ce8c3c805a
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785626B2
Reaction notes
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