Trifluoroacetic acid → [5-Cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid

HRID 2102191Notes

Reaction equation

HRID 2102191 reaction equation
[C:1]([C:3]1[C:4]([C:23]([F:26])([F:25])[F:24])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[C:7]([CH:20]1[CH2:22][CH2:21]1)=[CH:6]2)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:23]([F:26])([F:25])[F:24])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7]([CH:20]1[CH2:22][CH2:21]1)=[CH:6]2)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 711086661,1-Dimethylethyl [5-cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetate

Product 1

HCID 67406028[5-Cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,1-dimethylethyl [5-cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetate (Example 362A) (1.23 g, 4 mmol) in dry CH2Cl2 (10 mL) was added TFA (3.1 mL, 40 mmol) at rt. The mixture was stirred at rt overnight. Solvent and excess TFA were removed in vacuo. The residue was titrated with Et2O-hexanes to afford the title compound (1.05 g, 85%): MS (ES) m/z 309 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo

Sources & evidence

ORD record
ord-f92933bcb9494b9683c70cee9e228e5d
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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