Reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[CH:11][C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2.[Si:23]([O:30][CH2:31][CH2:32][CH2:33]Br)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C.O>[Si:23]([O:30][CH2:31][CH2:32][CH2:33][N:13]1[C:14]2[C:19](=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2)[CH:20]=[C:12]1[CH:11]=[CH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[Cl:3])([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:25])[CH3:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium hydride (1.05 g of a 50% dispersion in mineral oil, 0.022 mol) was added to a solution of the 2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indole prepared according to example 37 (4.13 g, 0.014 mol) in DMF (30 mL) and the solution was stirred at room temperature for 5 min. 3-Bromopropyl tert-butyl(dimethyl)silyl ether (4.04 g, 0.016 mol) was added and stirring was continued for 2 h. The solution was diluted with water, extracted with EtOAc which was washed well with brine and the organic phase was dried, the drying agent was removed and the solution was concentrated to dryness to give 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-2-[2-(2-chlorophenyl)ethenyl]-5-methoxy-1H-indole (28) as an oily solid (4.98 g) (as a mixture of E/Z isomers) which was used without further purification.
Workup
- customprepared
- stirringstirring
- waitwas continued for 2 h
- extractionextracted with EtOAc which
- washwas washed well with brine
- customthe organic phase was dried
- customthe drying agent was removed
- concentrationthe solution was concentrated to dryness
Sources & evidence
- ORD record
- ord-4c6ae40223f9402a82a15bbacc3512f7
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094798B1
Linked notes
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