Sodium Hydroxide → 6-(2,6-Difluorophenyl)-3-(4'-trifluoromethoxybiphenyl-4-yl)-[1,2,4]triazine

HRID 2085916Notes

Reaction equation

HRID 2085916 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][C:11]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[F:21])=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:36])([F:35])[O:24][C:25]1[CH:30]=[CH:29][C:28](OB(O)O)=[CH:27][CH:26]=1.C(=O)([O-])O.[Na+].[OH-].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[C:11]1[N:10]=[N:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]([F:22])([F:35])[F:36])=[CH:30][CH:29]=3)=[CH:3][CH:4]=2)=[N:13][CH:12]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 227270174-Trifluoromethoxyphenylboric acidHCID 227270223-(4-Bromophenyl)-6-(2,6-difluorophenyl)-[1,2,4]triazine

Product 1

HCID 227270266-(2,6-Difluorophenyl)-3-(4'-trifluoromethoxybiphenyl-4-yl)-[1,2,4]triazine

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

244 mg of 3-(4-bromophenyl)-6-(2,6-difluorophenyl)-[1,2,4]triazine are placed in 1.8 ml of 1,2-dimethoxyethane, and 2.5 mg of bis(triphenylphosphine)palladium(II) dichloride, 159 mg of 4-trifluoromethoxyphenylboric acid and 176 mg of sodium hydrogen carbonate in 1.8 ml of water are added in succession. The reaction mixture is then heated at 70° C. for 5 h. After cooling to room temperature, the suspension is poured into 1N sodium hydroxide solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product is dissolved in a minimum of hot ethyl acetate, filtered clear and crystallised at 0° C. In this way the title compound having a melting point of 199-202° C. is obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude product is dissolved in a minimum of hot ethyl acetate
  8. filtrationfiltered clear
  9. customcrystallised at 0° C
  10. customis obtained

Sources & evidence

ORD record
ord-af7f661c419e4ba2a5d2822bd3cadb51
Source dataset
uspto-grants-2004_04
Patent number
US06723720B2

Reaction notes

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