Trifluoroacetic acid → HCID 22240411, compound

HRID 2422967Notes

Reaction equation

HRID 2422967 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:19]([O:21]C(C)(C)C)=[O:20])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[N:9]=[C:8]([C:19]([OH:21])=[O:20])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22240455HCID 22240455, compound

Product 1

HCID 22240411HCID 22240411, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part C. To tert-butyl 5-(2-furyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate (1.0 g, 3.0 mmol) was added dichloromethane (7 mL) and trifluoroacetic acid (7 mL). The resulting black solution was maintained at rt under nitrogen for 2 h and was then concentrated to dryness. The resulting mixture was triturated with chloroform, and the remaining solid was washed with 50% hexanes in chloroform to afford 5-(2-furyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid (800 mg, 96%) as a light brown solid. 1H NMR (d6-DMSO) δ 7.75 (b m, 1H), 7.41 (d, 2H), 7.10 (d, 2H), 7.09 (s, 1H), 6.51 (br m, 1H), 6.09 (d, 1H), 3.84 (s, 3H).

Workup

  1. concentrationwas then concentrated to dryness
  2. customThe resulting mixture was triturated with chloroform
  3. washthe remaining solid was washed with 50% hexanes in chloroform

Sources & evidence

ORD record
ord-87573047f7f14e3ab32890a6c365b244
Source dataset
uspto-grants-2011_06
Patent number
US07960411B2

Reaction notes

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