Water → HCID 22316984, compound

HRID 396797Notes

Reaction equation

HRID 396797 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:18]=3)=[CH:15][C:14]([C:28](O)=[O:29])=[N:13]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].O.C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:12]2[C:16]([C:17]3[CH:18]=[CH:19][C:20]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)=[CH:21][CH:22]=3)=[CH:15][C:14]([CH2:28][OH:29])=[N:13]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 22316886HCID 22316886, compound

Product 1

HCID 22316984HCID 22316984, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[3-fluoro-4-(methylsulfonyl)phenyl]-5-[4-(2-furyl)phenyl]-1H-pyrazole-3-carboxylic acid (0.1 g, 0.235 mmol) in THF (2 mL) at 0° C. was added dropwise 1M borane-THF complex (0.7 mL). The mixture was stirred at room temperature for 3 hours. The solution was added water (1 mL) and ethyl acetate (20 mL), and the mixture was washed with 1N HCl, saturated NaHCO3, and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography eluting with hexane/ethyl acetate (1/1) to give the title compound (0.051 g, 52.6% yield).

Workup

  1. washthe mixture was washed with 1N HCl, saturated NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by flash chromatography
  6. washeluting with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-1c7c0e18b4f84547a23585d570ed9023
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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