Sodium hydride → 5-Bromo-1-(triisopropylsilyl)-1H-indole

HRID 1940541Notes

Reaction equation

HRID 1940541 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](OS(C(F)(F)F)(=O)=O)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>O1CCCC1>[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]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indoleYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromoindole (14.04 g, 72 mmol) in tetrahydrofuran (50 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in oil; 3.04 g, 76 mmol) in tetrahydrofuran (100 ml) and the resultant solution stirred for one hour at room temperature. Triisopropylsilyltrifluoromethane sulphonate (23.3 g, 76 mmol) was added slowly and the solution stirred for a further one hour. The reaction mixture was washed with sodium hydrogen carbonate solution, dried (MgSO4), and concentrated. The crude mixture was purified by flash chromatography, with hexane as eluant, to give 5-bromo-1-triisopropylsilyl-1H-indole (20.0 g, 79%) as a clear oil; δH (CDCl3) 1.10 (18H, d, J 8.4 Hz, 6× CH3), 2.70 (3H, m, 3×CH), 6.55 (1H, d, J 3.9 Hz, ArH), 7.20 (2H, m, ArH), 7.35 (1H, d, J 8.5 Hz, ArH), and 7.75 (1H, d, J 1.4 Hz, ArH).

Workup

  1. washThe reaction mixture was washed with sodium hydrogen carbonate solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude mixture was purified by flash chromatography, with hexane as eluant

Sources & evidence

ORD record
ord-c3d3ebbac85546a6ab21c5e6e2074513
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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