Sodium hydride → HCID 67300756, compound

HRID 1015433Notes

Reaction equation

HRID 1015433 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1>CN(C)C=O>[CH2:1]([C:3]1[N:4]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=2)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 67300353HCID 67300353, compound

Product 1

HCID 67300756HCID 67300756, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500 mg portion of ethyl 2-ethyl-3-methyl-1H-indole-5-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and 113 mg of sodium hydride (55% dispersion in oil) was added under ice-cooling, followed by stirring at room temperature for 30 minutes. Then, 490 mg of 1-(bromomethyl)-4-fluorobenzene was added under ice-cooling, followed by stirring at room temperature for 2 hours. After evaporation of the solvent under a reduced pressure, the residue was diluted with ethyl acetate and washed with water and saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20 to 1:0) to obtain 587 mg of ethyl 2-ethyl-1-(4-fluorobenzyl)-3-methyl-1H-indole-5-carboxylate as a pale brown oily material.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 2 hours
  4. customAfter evaporation of the solvent under a reduced pressure
  5. additionthe residue was diluted with ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20 to 1:0)

Sources & evidence

ORD record
ord-f03bfc3af19740e8855c4edf4ca85509
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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