Dimethylformamide → 2-[6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N,N-dimethyl-acetamide

HRID 505072Notes

Reaction equation

HRID 505072 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][CH:3]=1.[H-].[Na+].[CH3:19][N:20]([CH2:22][C:23](Cl)=O)[CH3:21].CN(C=[O:30])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[CH2:23][C:22]([N:20]([CH3:21])[CH3:19])=[O:30])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 70103442-(Dimethylamino)acetyl chlorideHCID 224972521-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone

Product 1

HCID 667442552-[6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N,N-dimethyl-acetamideYield 61%

Procedure

To a stirred solution of 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (0.75 g) in 20 ml of DMF at 0° C., were added 128 mg (1.1 eq.) of NaH (60% in oil). The mixture was stirred for 30 min. and then 0.32 ml (1.1 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 598 mg (61%) of 2-[6-chloro-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-8c3e4cdfe69f4f969f4afd9d75cd167c
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

Loading…