Sodium hydride → HCID 24785925, compound

HRID 625985Notes

Reaction equation

HRID 625985 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1)[CH3:4].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](F)[N:16]=1>CS(C)=O>[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([F:14])[N:16]=2)=[C:7]([O:12][CH3:13])[CH:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 624654-EthylguaiacolHCID 739342,6-Difluoropyridine

Product 1

HCID 24785925HCID 24785925, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of NaH (1.2 mmol; 50 mg) in anhydrous DMSO (1 mL) under argon, was added 4-ethyl-2-methoxyphenol (1 mmol; 152.2 mg) followed by 2,6-difluoropyridine (1 mmol; 0.1 ml). The reaction mixture was stirred at 120° C. overnight. After quenching with NaOH (0.1N; 3 mL), the mixture was extracted with dichloromethane (3*5 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo, to give the title compound as a light yellow oil (250 mg; 1 mmol; 100%), used without further purification.

Workup

  1. customAfter quenching with NaOH (0.1N; 3 mL)
  2. extractionthe mixture was extracted with dichloromethane (3*5 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ca2cff3541540f481f493addd9a9a82
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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