Sodium hydride → 2-[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N-methyl-acetamide

HRID 898144Notes

Reaction equation

HRID 898144 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+].Cl[CH2:20][C:21]([NH:23][CH3:24])=[O:22]>CN(C=O)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[CH2:20][C:21]([NH:23][CH3:24])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 667732-chloro-N-methylacetamideHCID 224972521-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone

Product 1

HCID 667442882-[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (described previously in U.S. 2004067939) in DMF were added 2.1 eq. NaH (60% in oil). The mixture was stirred at RT for 30 min. and then the (commercially available) 2-chloro-N-methyl-acetamide (1.1 eq.) was added. The mixture was stirred an additional 14 hours at 60° C. and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Purification by preparative HPLC gave the title compound.

Workup

  1. stirringThe mixture was stirred an additional 14 hours at 60° C.
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-4ad8d23b41464c21b191944e6ba5cf8c
Source dataset
uspto-grants-2008_04
Patent number
US07351706B2

Reaction notes

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