Tetrabutylammonium Fluoride → 1-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid

HRID 413694Notes

Reaction equation

HRID 413694 reaction equation
C[Si](CC[O:7][C:8]([C:10]1[C:11]([NH:21][C:22]([O:24][CH2:25][C:26]2[O:27][C:28]3[CH:34]=[CH:33][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:31][C:29]=3[CH:30]=2)=[O:23])=[N:12][N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)=[O:9])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C>[C:15]1([N:13]2[CH:14]=[C:10]([C:8]([OH:9])=[O:7])[C:11]([NH:21][C:22]([O:24][CH2:25][C:26]3[O:27][C:28]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:31][C:29]=4[CH:30]=3)=[O:23])=[N:12]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 113303421-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid trimethylsilylethyl ester

Product 1

HCID 101612631-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acidYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid trimethylsilylethyl ester (1.27 g, 2.29 mmol) in 10 mL DMF under N2, was added tetra-n-butylammonium fluoride (2.75 mL of 1M THF solution, 2.75 mmol). The mixture was allowed to stir at room temp. for 2 hrs. The solvent was evaporated under high vacuum (60° C. max). Water was added and the mixture was extracted. After addition of 4 mL 1N HCl a white precipitate separated which was filtered off. This material was triturated in 10 mL boiling EtOH to afford 684 mg of 1-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid as a white solid, mp 220.6°-220.8° C.

Workup

  1. customThe solvent was evaporated under high vacuum (60° C. max)
  2. additionWater was added
  3. extractionthe mixture was extracted
  4. additionAfter addition of 4 mL 1N HCl a white precipitate
  5. customseparated which
  6. filtrationwas filtered off
  7. customThis material was triturated in 10 mL

Sources & evidence

ORD record
ord-e94c2ab6cd3543c99788ee5017a31d19
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Reaction notes

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