Sodium hydride → HCID 22926878, compound

HRID 1985422Notes

Reaction equation

HRID 1985422 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O.O>[CH2:20]([O:19][CH2:18][CH2:17][N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 22926878HCID 22926878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.75 g of Methyl 1H-indol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and 0.7 g of 60% sodium hydride was added under ice-cooling. The reaction solution was stirred at room temperature for 30 minutes, treated with 2.5 ml of benzyl 2-bromoethyl ether, and stirred at room temperature for a further 2 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 (8% ethyl acetate-hexane), to give 3.6 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-66563155d79b45228671337228989996
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

Loading…