Sodium hydride → HCID 131718226, compound

HRID 1656293Notes

Reaction equation

HRID 1656293 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[Si:13]([O:20][CH2:21][CH2:22]Br)([C:16](C)(C)C)([CH3:15])C>CN(C=O)C>[CH2:5]([CH:21]([O:20][SiH:13]([CH3:15])[CH3:16])[CH2:22][N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[CH2:4][CH2:12][CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 131718226HCID 131718226, compoundYield 151.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of sodium hydride (12 g, 0.3 mol, 60% dispersion in oil) in DMF (200 mL) was added dropwise a solution of 5-bromoindole (50 g, 0.255 mol) in DMF (300 mL). After stirring for 15 minutes 2-t-butyldimethylsilyloxyethyl bromide (60 g, 0.255 mol, neat) was added dropwise and the reaction mixture stirred for 1 hour. The reaction mixture was partitioned between ice water and ethyl ether. The organic fraction was washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by column chromatography (silica, 3:1 hexane/acetone) to give 68.6 g of the title compound as a light yellow oil.

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was partitioned between ice water and ethyl ether
  3. washThe organic fraction was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by column chromatography (silica, 3:1 hexane/acetone)

Sources & evidence

ORD record
ord-c4af173f9f884a0ba9ec2cd86018852f
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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