Water → HCID 23090593, compound

HRID 1437218Notes

Reaction equation

HRID 1437218 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20](O)=[O:21])=[N:10]2)=[CH:5][CH:4]=1.O.C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([CH2:20][OH:21])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 23090164HCID 23090164, compound

Product 1

HCID 23090593HCID 23090593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an argon atmosphere while cooling with ice, 1.08M borane-tetrahydrofuran complex in tetrahydrofuran (9.2 mL) was added dropwise to 1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carboxylic acid (1.181 g) in tetrahydrofuran (20 mL) obtained from Referential Example 41 over a period of 10 minutes, and the resultant mixture was stirred at room temperature for 7 hours. Water and ethyl acetate were added to the reaction mixture, followed by stirring, and precipitated insoluble matter was removed by filtration, and then an organic layer was separated. The organic layer was sequentially washed with water and saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as an oily product (682 mg, 60%).

Workup

  1. customprecipitated insoluble matter
  2. customwas removed by filtration
  3. customan organic layer was separated
  4. washThe organic layer was sequentially washed with water and saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4bc8d43bda1643dca5c4b5bb40d301fe
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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