Propargyl bromide → HCID 22927001, compound

HRID 1985427Notes

Reaction equation

HRID 1985427 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2]1.[H-].[Na+].[CH2:23](Br)[C:24]#[CH:25].[Cl-].[NH4+]>CN(C)C=O.O>[CH:18]([O:17][CH:11]([CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:25][C:24]#[CH:23])[CH:2]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22927039HCID 22927039, compound

Product 1

HCID 22927001HCID 22927001, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.23 g of Ethyl 3-(1H-indol-3-yl)-2-isopropoxypropionate was dissolved in 5 ml of N,N-dimethylformamide, and 34 mg of 60% sodium hydride was added under ice-cooling. The reaction solution was stirred for 30 minutes under ice-cooling, then 0.09 ml of propargyl bromide was added, and stirring was continued at room temperature for 16 hours. The reaction solution was cooled with ice, treated with water and ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography (9% ethyl acetate-hexane), to give 0.18 g of the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. waitwas continued at room temperature for 16 hours
  5. temperatureThe reaction solution was cooled with ice
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-1995bd39c5d74608a877c3f2d32e91ec
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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