Water → HCID 86760870, compound

HRID 1982985Notes

Reaction equation

HRID 1982985 reaction equation
Cl[CH2:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1.[F:14][C:15]([F:24])([F:23])[CH2:16][CH2:17][CH:18]([C:21]#[N:22])[C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:3]([CH2:2][C:18]([CH2:17][CH2:16][C:15]([F:14])([F:23])[F:24])([C:19]#[N:20])[C:21]#[N:22])[CH:4]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 23149209HCID 23149209, compound

Product 1

HCID 86760870HCID 86760870, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.02 g of 1-(chloromethyl)-3-formyl-1H-indole and 2.53 g of (3,3,3-trifluoropropyl) malononitrile were dissolved in 45 ml of N,N-dimethylformamide. 4.35 g of potassium carbonate was added to the solution under ice cooling with stirring, followed by stirring at room temperature for 3 hours. Water was added to the reaction mixture, and then extracted with MTBE. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.68 g of [{3-formyl-1H-indole-1-yl}methyl](3,3,3-trifluoropropyl)malononitrile(referred to as the compound of the present invention (40), hereinafter) shown by below formula.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionextracted with MTBE
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b287bb5311a4abb88ec7684c72d5953
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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