Water → HCID 23157283, compound

HRID 2110856Notes

Reaction equation

HRID 2110856 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]([O:21][CH2:22][CH2:23]Cl)[CH3:20].O>CN(C)C=O>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:20][CH2:19][O:21][CH2:22][CH3:23])[C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 231573293-Bromo-2-phenyl-1H-indole

Product 1

HCID 23157283HCID 23157283, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, sodium hydride (60% in oil, 0.48 g, 12.0 mmol) was added to a solution of 3-bromo-2-phenyl-1H-indole (2.72 g, 10.0 mmol) in N,N-dimethylformamide (10 mL) by small portions, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 30 min. 2-Chloroethyl ethyl ether (1.65 mL, 15.0 mmol) was added to the reaction mixture, and the mixture was stirred at 70° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane) to give the title compound (2.60 g, yield 76%) as a red oil. MS: m/z 344 (MH+).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at 70° C. for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-90a6d4c15ffd4678b3887ddbb1a39c9e
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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