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Tetrabutylammonium Fluoride → 5-Amino-1-(4-fluorophenyl)4-[3-(2-hydroxyethyl)benzoyl]pyrazole

HRID 429363
Notes
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Reaction equation

HRID 429363 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[CH:16]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][OH:23])[CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 116045845-Amino-1-(4-fluorophenyl)-4-[3-(2-tert-butyldimethylsiloxyethyl)benzoyl]pyrazole

Product 1

HCID 98402635-Amino-1-(4-fluorophenyl)4-[3-(2-hydroxyethyl)benzoyl]pyrazoleYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 57417360
Sodium chloride; water
Solvent

Procedure

To a solution of 5-amino-1-(4-fluorophenyl)-4-[3-(2-tert-butyldimethylsiloxyethyl)-benzoyl]pyrazole (1.2 g, 3.0 mmol) in tetrahydrofuran (25 ml) was added tetrabutylammonium fluoride (3.6 ml, 3.6 mmol, 1 M solution in tetrahydrofuran). After 1 h, the reaction mixture was poured into brine and the product was extracted into ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 40-100% ethyl acetate/hexane) to give 5-amino-1-(4-fluorophenyl)-4-[3-(2-hydroxyethyl)benzoyl]pyrazole (0.8 g).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (elution gradient: 40-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e9e61ce9fe8f448fb260b25263ca467d
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06316466B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes