Sodium hydride → 5-Bromo-1-(triisopropylsilyl)-1H-indole
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5-Bromoindole (1.4 gm, 7.14 mmol) was dissolved in dry THF (50 ml) and cooled to 0° C., which was followed by the addition of NaH (0.34 g, 14.28 mmol) portion wise. The reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was again cooled to 0° C. and triisopropylsilyl chloride (1.78 g, 9.28 mmol) was added drop wise. The mixture was allowed to warm to room temperature and was stirred overnight. The solvent was evaporated under reduced pressure and triturated with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml) and dried over Na2SO4 and evaporated. The compound was purified by flash column chromatography using pure hexanes to afford colorless oily product 47 (1.90 g, 76%). 1H NMR (400 MHz, CDCl3) δ 1.13 (d, 18H, J=8.0 Hz), 1.63-1.71 (m, 3H), 6.56 (d, 1H, J=3.2 Hz), 7.20-7.25 (m, 2H), 7.37 (d, 1H, J=8.8 Hz), 7.74 (d, 1H, J=2.0 Hz).
Workup
- temperatureThe reaction mixture was again cooled to 0° C.
- temperatureto warm to room temperature
- stirringwas stirred overnight
- customThe solvent was evaporated under reduced pressure
- customtriturated with ethyl acetate (100 ml)
- washThe organic layer was washed with brine (50 ml)
- dry with materialdried over Na2SO4
- customevaporated
- customThe compound was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-e5f1d7bf0f5543349231b0ac9a2ed9b4
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034877B2
Reaction notes
Loading…