Water → HCID 58244200, compound

HRID 389156Notes

Reaction equation

HRID 389156 reaction equation
[OH-].[K+].Br[C:4]1[CH:5]=[C:6]([C:10]2[N:14]([CH3:15])[C:13]([C:16]([CH3:28])([O:18][C:19]3[C:24]([F:25])=[CH:23][C:22]([F:26])=[CH:21][C:20]=3[F:27])[CH3:17])=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1.C(Cl)(Cl)Cl.O.[CH3:34][N:35]1C(=O)CCC1>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][N:14]1[C:13]([C:16]([CH3:28])([O:18][C:19]2[C:24]([F:25])=[CH:23][C:22]([F:26])=[CH:21][C:20]=2[F:27])[CH3:17])=[N:12][N:11]=[C:10]1[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:34]#[N:35]

Participants

8

Reactant 5

HCID 962WaterHCID 6212ChloroformHCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 58244000HCID 58244000, compound

Product 1

HCID 58244200HCID 58244200, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

Zinc cyanide (118 mg), potassium hydroxide (75 mg) and tetrakis(triphenylphosphine)palladium (0) (290 mg) were sequentially added to a solution of 3-(3-bromophenyl)-4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazole (356 mg) in NMP (5 ml) under an argon atmosphere, followed by stirring at 100° C. for 3 hours. Chloroform and water were added to the reaction solution, the precipitated solid was separated by celite filtration, followed by extraction. The organic layer was washed with a 1M aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 0:100), and the solvent was evaporated under reduced pressure. The residue was solidified with diisopropylether and washed under heating to obtain, as a colorless powdery solid, 3-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzonitrile (238 mg).

Workup

  1. customthe precipitated solid was separated by celite filtration
  2. extractionfollowed by extraction
  3. washThe organic layer was washed with a 1M aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 0:100)
  7. customthe solvent was evaporated under reduced pressure
  8. washwashed
  9. temperatureunder heating

Sources & evidence

ORD record
ord-60b54bb8f75f41ba92db51ce84689174
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

Loading…