Dimethylformamide → HCID 59657572, compound

HRID 1865933Notes

Reaction equation

HRID 1865933 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][NH:8]2)=[CH:4][C:3]=1[CH3:17].[H-].[Na+].[CH3:20][N:21]([CH2:23][C:24](Cl)=O)[CH3:22].CN(C=[O:31])C>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7][N:8]2[CH2:24][C:23]([N:21]([CH3:22])[CH3:20])=[O:31])=[CH:4][C:3]=1[CH3:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 70103442-(Dimethylamino)acetyl chlorideHCID 59657558HCID 59657558, compound

Product 1

HCID 59657572HCID 59657572, compoundYield 60%

Procedure

To a stirred solution of 1-(6-chloro-5methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (0.38 g) in 10 ml of DMF at 0° C. were added 64 mg (1.1 eq.) of NaH (60% in oil). After stirring the mixture for 30 min. were added 0.16 ml (1.1 eq.) of dimethylamino-acetyl chloride. The mixture was stirred for an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo to afford 300 mg (60%) of the title compound as a white solid.

Workup

  1. stirringThe mixture was stirred for an additional hour
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1a7438df4e74307b287156cc6c19421
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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