HCID 21090797, compound → HCID 21090796, compound

HRID 351267Notes

Reaction equation

HRID 351267 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([C:18]3[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[N:16]=[C:15]([CH:26]([F:28])[F:27])[CH:14]=2)=[CH:9][CH:8]=1)(=O)C>C1COCC1.CO>[F:28][CH:26]([F:27])[C:15]1[CH:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][OH:4])=[CH:8][CH:9]=2)[N:17]([C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[N:16]=1

Participants

4

Reactant 1

HCID 21090797HCID 21090797, compound

Product 1

HCID 21090796HCID 21090796, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{4-[3-(difluoromethyl)-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate (10 g) in THF (120 ml) and MeOH (30 ml) was added 1NNaOH (60 ml) at room temperature. The reaction mixture was stirred at the same temperature for 4 hrs, and then neutralized with 1NHCl (60 ml), evaporated, and extracted twice with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered and evaporated to give crude product. The residue was column chromatographed on silica gel and crystalized from IPE and filtered to give 3.0 g of 2-{4-[3-(difluoromethyl)-1-(6-methoxy-3-pyridinyl)-1-H-pyrazol-5-yl]phenyl}ethanol. The filtrate was evaporated and filtered to give 4.65 g of second crystal.

Workup

  1. customevaporated
  2. extractionextracted twice with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customchromatographed on silica gel
  9. customcrystalized from IPE
  10. filtrationfiltered

Sources & evidence

ORD record
ord-c408c2c69aeb4057bca2256eff6cac6d
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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