Sodium hydride → HCID 69456027, compound

HRID 1351988Notes

Reaction equation

HRID 1351988 reaction equation
[H-].[Na+].[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)([CH3:6])([CH3:5])[CH3:4].[Br-].[C:21](#[N:23])[CH3:22]>CN(C)C=O.[Cl-].[Na+].O.O>[Si:7]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:22][C:21]#[N:23])([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 115939764-(t-Butyldimethylsilyloxy)indoleHCID 22916878HCID 22916878, compound

Product 1

HCID 69456027HCID 69456027, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere, to a suspension of sodium hydride (60% dispersion in mineral oil, 750 mg, 18.8 mmol) in dimethyl-formamide (30 mL) is added dropwise a solution of 4-{[tert-butyl-(dimethyl)silyl]oxy}-1H-indole (2.32 g, 9.38 mmol) in dimethylformamide (10 mL)-with stirring under ice-cooling, and the mixture is stirred at the same temperature for 15 minutes. To the mixture is added dropwise acetonitrile bromide (1.96 mL, 28.1 mmol), and the mixture is stirred at room temperature for 15 hours. The reaction mixture is diluted with a mixture of a saturated brine and water (1:1, 400 mL), and the mixture is extracted with ethyl acetate (2×100 mL). The combined organic layer is washed with a mixture of a saturated brine and water (1:1, 100 mL), dried over anhydrous potassium carbonate, and filtered. The filtrate is concentrated under reduced pressure, and the obtained residue is purified by silica gel column (ethyl acetate:hexane=10:1→5:1) to give the title compound as a pale brown solid (803 mg, yield: 39%).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 15 minutes
  3. stirringthe mixture is stirred at room temperature for 15 hours
  4. extractionthe mixture is extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic layer is washed with a mixture of a saturated brine and water (1:1, 100 mL)
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customthe obtained residue is purified by silica gel column (ethyl acetate:hexane=10:1→5:1)

Sources & evidence

ORD record
ord-9a13249d5dbd4ee2aba9ed1f4f5d24ba
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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