Pyrazole → HCID 61229381, compound

HRID 491274Notes

Reaction equation

HRID 491274 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](F)[N:10]=1>CN(C=O)C.C1COCC1.O>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)[N:10]=1

Participants

7

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 739342,6-Difluoropyridine

Product 1

HCID 61229381HCID 61229381, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride / 60 percent oil dispersion (0.80 g, 20 mmol) was added over 5 minutes to a solution of pyrazole (1.4 g, 20 mmol) in DMF (20 mL) and THF (6 mL). After 10 minutes, 2,6-difluoropyridine (1.9 mL, 21 mmol) was added in one portion. After stirring for 20 h, the reaction was diluted with water (250 mL) and extracted with ether (5×50 mL). The organics were combined, washed with water (3×50 mL), brine (50 mL) and dried (Na2SO4). Filtration and removal of solvent left a gold oil that was purified by reverse phase liquid chromatography, affording product as a colorless oil, 2.0 g, 12.3 mmol, 61 percent yield.

Workup

  1. extractionextracted with ether (5×50 mL)
  2. washwashed with water (3×50 mL), brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationFiltration and removal of solvent
  5. waitleft a gold oil that
  6. customwas purified by reverse phase liquid chromatography
  7. customaffording product as a colorless oil, 2.0 g, 12.3 mmol, 61 percent yield

Sources & evidence

ORD record
ord-63ef1b0116f14894a7f60dac6248cac3
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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