Trifluoroacetic acid → 3-(3,5-dichlorophenyl)-1-[4-(methoxycarbonyl)benzyl]-1H-pyrazole-5-carboxylic acid

HRID 1865415Notes

Reaction equation

HRID 1865415 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([O:16]C(C)(C)C)=[O:15])[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86620043tert-Butyl 3-[3,5-dichlorophenyl)-1-[4-(methoxycarbonyl)benzyl]-1H-pyrazole-5-carboxylate

Product 1

HCID 579755303-(3,5-dichlorophenyl)-1-[4-(methoxycarbonyl)benzyl]-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from step E (5.54 g, 12 mmol) in 30 mL of dichloromethane was added 13 mL of trifluoroacetic acid. The reaction mixture was stirred at ambient temperature for 16 h then was concentrated in vacuo and excess trifluoroacetic acid removed by azeotropic distillation with dichloromethane to provide the title compound as a white solid. 1H NMR (500 MHz, CDCl3) δ; 8.00 (d, J=8.2 Hz, 2H); 7.83 (d, J=1.8 Hz, 2H); 7.41 (d, J=1.9 Hz, 1H); 7.36 (d, J=8.3 Hz, 2H); 7.32 (s, 1H); 5.94 (s, 2H); 4.87 (s, 3H).

Workup

  1. concentrationthen was concentrated in vacuo and excess trifluoroacetic acid
  2. customremoved by azeotropic distillation with dichloromethane

Sources & evidence

ORD record
ord-ea3b1b3522e24fa1bd475ad0e990aad2
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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