Dimethylformamide → HCID 66743700, compound

HRID 505077Notes

Reaction equation

HRID 505077 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[C:12](=[O:17])[C:13]([F:16])([F:15])[F:14].[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:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([CH2:24][C:23]([N:21]([CH3:22])[CH3:20])=[O:31])[CH:6]=[C:5]2[C:12](=[O:17])[C:13]([F:14])([F:15])[F:16]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 70103442-(Dimethylamino)acetyl chlorideHCID 66743709HCID 66743709, compound

Product 1

HCID 66743700HCID 66743700, compoundYield 78%

Procedure

To a stirred solution of 1-(5,6-dichloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (0.11 g) in 3 ml of DMF at 0° C., were added 18 mg (1.05 eq.) of NaH (60% in oil). The mixture was stirred for 30 min. and then 0.04 ml (1.0 eq.) of dimethylamino-acetyl chloride were added. The mixture was stirred 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 112 mg (78%) of 2-[5,6-dichloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N,N-dimethyl-acetamide as a white solid.

Workup

  1. stirringThe mixture was stirred 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-2f3fb52b15104c7a88be2cd93301287c
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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