Trifluoroacetic acid → HCID 57800403, compound

HRID 913409Notes

Reaction equation

HRID 913409 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:22]([F:24])[F:23])[N:6]2[CH:13]([CH3:21])[C:14]([O:16]C(C)(C)C)=[O:15].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:22]([F:23])[F:24])[N:6]2[CH:13]([CH3:21])[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57800183HCID 57800183, compound

Product 1

HCID 57800403HCID 57800403, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 2-[4-chloro-5-cyano-2-(difluoromethyl)-1H-indol-1-yl]propanoate (0.072 g, 0.2 mmol) in CH2Cl2 (5 mL) was added TFA (5 mL) and stirred at rt for 4 h. The mixture was concentrated in vacuo. The residue was diluted with Et2O and hexane was added while stirring. The solids were collected by filtration and washed with hexane to afford the title compound as a white solid (0.058 g, 95% yield): MS (ES) m/z 299 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue was diluted with Et2O and hexane
  3. additionwas added
  4. stirringwhile stirring
  5. filtrationThe solids were collected by filtration
  6. washwashed with hexane

Sources & evidence

ORD record
ord-b736310f4b264cd1bb3dc17df02ffb9d
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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