Trifluoroacetic acid → 5-cyano-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

HRID 2401173Notes

Reaction equation

HRID 2401173 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([C:12]([O:14]C(C)(C)C)=[O:13])=[C:10]([C:19]([F:22])([F:21])[F:20])[NH:9][C:6]2=[N:7][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([C:12]([OH:14])=[O:13])=[C:10]([C:19]([F:22])([F:20])[F:21])[NH:9][C:6]2=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 699286821,1-dimethylethyl 5-cyano-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate2×

Product 1

HCID 671123375-cyano-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acidYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 5-cyano-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (Intermediate 2, 2.77 g, 8.90 mmol) was dissolved in DCM (40 mL), treated with TFA (10 mL) and the resulting mixture was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure to give the title compound as a brown solid (2.49 g);

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-870652248bca41acaee457e7688552dd
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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