Dimethylformamide → HCID 58243511, compound

HRID 389115Notes

Reaction equation

HRID 389115 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])=[N:7][N:6]=[C:5]1[CH:19]([OH:21])[CH3:20].CN(C=O)C.Cl[C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[CH:30][N:29]=1>C(Cl)(Cl)Cl.O>[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:16])([F:18])[F:17])=[N:7][N:6]=[C:5]1[CH:19]([O:21][C:28]1[N:29]=[CH:30][CH:31]=[CH:32][C:33]=1[C:34]#[N:35])[CH3:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 810792-ChloronicotinonitrileHCID 58243956HCID 58243956, compound

Product 1

HCID 58243511HCID 58243511, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Sodium hydride (53 mg) was added to a mixture of 1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethanol (300 mg) and DMF (10 ml) at room temperature, followed by stirring for 10 minutes, and 2-chloro-3-cyanopyridine (153 mg) was added thereto, followed by stirring at room temperature for 13 hours. Water and chloroform were added to the reaction solution, followed by separation operation, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain, as a light yellow amorphous product, 2-(1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)nicotinonitrile (306 mg).

Workup

  1. stirringby stirring at room temperature for 13 hours
  2. customfollowed by separation operation
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-2dc60f8afc634d729ae0e878a58d7c3f
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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