Sodium hydride → HCID 86651031, compound

HRID 1510092Notes

Reaction equation

HRID 1510092 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Br[CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1>CN(C=O)C>[Cl:1][C:2]1[N:3]([CH:21]2[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1370573-BromocyclohexeneHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 86651031HCID 86651031, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-chloro-1H-indole-3-carbaldehyde (2.00 g, 11.1 mmol) in DMF (15 ml) was added sodium hydride (468 mg, 11.7 mmol, 60% dispersion in mineral oil). Under an argon atmosphere, the suspension was stirred at 40° C. for 20 min and then allowed to cool to room temperature. After the addition of 3-bromocyclohexene (2.56 ml, 22.3 mmol) the reaction mixture was stirred at room temperature for 1 h. The mixture was then quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was and purified by silica gel chromatography (EA/HEP 1:10). 1.13 g of the title compound were obtained.

Workup

  1. temperatureto cool to room temperature
  2. stirringwas stirred at room temperature for 1 h
  3. customThe mixture was then quenched with water
  4. extractionextracted with EA
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. custompurified by silica gel chromatography (EA/HEP 1:10)

Sources & evidence

ORD record
ord-45a4bfabbd41494d881c76e88873108f
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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