Ethyl Bromide → HCID 18007603, compound

HRID 1934594Notes

Reaction equation

HRID 1934594 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.Br[CH2:14][CH3:15]>CN(C)C=O>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:14][CH3:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 6764936-Bromoindole

Product 1

HCID 18007603HCID 18007603, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (480 mg of a 60% dispersion in mineral oil) was added to a stirred solution of 6-bromoindole (1.8 g, 9.2 mmol) in dimethylformamide (20 ml) at 0° C. under a nitrogen atmosphere. After 1 hour bromoethane (1.1 ml, 14.7 mmol) was added and the cooling bath removed. After 12 hours the dimethylformamide was removed in vacuo. The residue was purified directly by flash column chromatoraphy (using 95% hexane, 5% ethyl acetate as eluant) to give 2.1 g of the subtitle compound as a yellow oil.

Workup

  1. customthe cooling bath removed
  2. customAfter 12 hours the dimethylformamide was removed in vacuo
  3. customThe residue was purified directly by flash column chromatoraphy (using 95% hexane, 5% ethyl acetate as eluant)

Sources & evidence

ORD record
ord-c32c899fa7ed44b0bc58b1736d273707
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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