3,4-dihydro-2H-pyran → HCID 59023068, compound

HRID 1921840Notes

Reaction equation

HRID 1921840 reaction equation
[Br:1][C:2]1[C:3]([C:7]#[N:8])=[N:4][NH:5][CH:6]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.[H-].[Na+]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)[C:3]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 24758Sodium hydrideHCID 27356234-Bromo-1H-pyrazole-3-carbonitrile

Product 1

HCID 59023068HCID 59023068, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Conditions

Temperature
95 °C

Procedure

4-Bromo-1H-pyrazole-3-carbonitrile (150 mg, 0.87 mmol) is dissolved in 3,4-dihydro-2H-pyran (25 mL, 2.6 mmol) in the presence of a catalytic amount of TFA (1 mg, 0.009 mmol). The reaction mixture is stirred at 95° C. for 1 hour, cooled and then quenched using NaH (1.2 mg, 0.052 mmol). After removing the solvent, the residue is purified by silica gel column chromatography eluting with a mixture of 3:1 petroleum ether-dichloromethane, followed by 10:1 petroleum ether-ethyl acetate. The fractions containing the desired compounds are collected and concentrated in vacuo to afford the title compound as a colorless oil (90 mg, 40%).

Workup

  1. temperaturecooled
  2. customquenched
  3. customAfter removing the solvent
  4. customthe residue is purified by silica gel column chromatography
  5. washeluting with a mixture of 3:1 petroleum ether-dichloromethane
  6. additionThe fractions containing the desired compounds
  7. customare collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b16588549b3b466d9c1e0414a614b24c
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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