4-Bromobutyronitrile → HCID 70030611, compound

HRID 396194Notes

Reaction equation

HRID 396194 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:28][CH2:29][CH2:30][C:31]#[N:32]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:28][CH2:29][CH2:30][C:31]#[N:32])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 214124-BromobutyronitrileHCID 24758Sodium hydrideHCID 18412777HCID 18412777, compound

Product 1

HCID 70030611HCID 70030611, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid ethyl ester (1.50 g, 4.12 mmol) in dimethylformamide (15 mL) was added 60% sodium hydride (0.25 g, 6.18 mmol). The reaction mixture was stirred at ambient temperature under argon for 2.5 h. 4-Bromobutyronitrile (0.92 g, 6.14 mmol) was then added and the reaction mixture stirred for another 14 h at ambient temperature. The reaction was diluted with ethyl acetate and washed three times with water. The organic layer was dried over MgSO4, filtered and the solvent removed under reduced pressure. Purification by flash chromatography (silica gel, 25% ethyl acetate/hexane) yielded an off-white solid (1.60 g, 95%). MS(ES) m/e 431.0 [M +H]+.

Workup

  1. stirringthe reaction mixture stirred for another 14 h at ambient temperature
  2. washwashed three times with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customPurification by flash chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2feb76a4f8784b26b4204d4b8bc98f06
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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