Water → HCID 50970819, compound

HRID 1777389Notes

Reaction equation

HRID 1777389 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1.F[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C(#N)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([N:1]2[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]2)=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27628712,5-DifluoropyridineHCID 42936042-(1H-Pyrazol-4-yl)ethanol

Product 1

HCID 50970819HCID 50970819, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(1H-pyrazol-4-yl)ethanol (1.0 g, 8.9 mmol) and 2,5-difluoropyridine (0.89 mL, 9.8 mmol) in acetonitrile (45 mL), Cs2CO3 (9.7 g, 17.8 mmol) was added, and the resulting mixture was stirred for 3 hours at 80° C. The reaction mixture was allowed to cool, then water was added thereto, followed by extraction with EtOAc. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over Na2SO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 25 g, hexane/EtOAc=90/10 to 30/70) to obtain the title compound (0.63 g) (colorless solid).

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over Na2SO4
  5. filtrationthe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by column chromatography (HP-Sil 25 g, hexane/EtOAc=90/10 to 30/70)

Sources & evidence

ORD record
ord-7e5651ccabf74eddbb4868298b7bc9b4
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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