Tetrabutylammonium Fluoride → 3-[2-(3-Hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276952Notes

Reaction equation

HRID 276952 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([C:22]3[C:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=34)=[N:16]2)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([C:22]3[C:23]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=34)=[N:16]2)[CH2:10]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 226291913-[2-{3-(Tert-butyldimethylsilyloxy)cyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 226292043-[2-(3-Hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 97.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[2-{3-(tert-butyldimethylsilyloxy)cyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (570 mg) and 70% aqueous tetrabutylammonium fluoride (4.3 g) in tetrahydrofuran (10 ml) was stirred for overnight at room temperature. A reaction mixture was diluted with ethyl acetate (100 ml), which was washed in turn with water (50 ml×4) and saturated sodium chloride in water (50 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (40 ml) eluting in turn with 30%, 50% ethyl acetate in dichloromethane and ethyl acetate. Fractions containing desired product were concentrated under reduced pressure to give residue, which was recrystallized from ethanol to give 3-[2-(3-hydroxycyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (430 mg).

Workup

  1. washwas washed in turn with water (50 ml×4) and saturated sodium chloride in water (50 ml×2)
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (40 ml)
  6. washeluting in turn with 30%, 50% ethyl acetate in dichloromethane and ethyl acetate
  7. additionFractions containing desired product
  8. concentrationwere concentrated under reduced pressure
  9. customto give residue, which
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-1b3b5652a39547f282010dcdcbdd20e1
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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