Toluene → HCID 68014904, compound

HRID 1747793Notes

Reaction equation

HRID 1747793 reaction equation
FC(F)(F)S(O[C:7]1[C:12](=[O:13])[CH:11]=[N:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH:8]=1)(=O)=O.[C:26]1([N:32]2[C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=[N:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O.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.C(O)C>[C:26]1([N:32]2[C:36]([C:7]3[C:12](=[O:13])[CH:11]=[N:10][N:9]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=4)[CH:8]=3)=[CH:35][CH:34]=[N:33]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 89586574HCID 89586574, compound

Product 1

HCID 68014904HCID 68014904, compoundYield 8.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

5-oxo-2-[3-(trifluoromethyl)phenyl]-2,5-dihydropyridazin-4-yl trifluoromethanesulfonate (0.100 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.139 g), sodium carbonate (0.109 g) and tetrakis(triphenylphosphine)palladium(0) (0.0298 g) were suspended in a mixed solvent of toluene (2.06 mL), ethanol (0.52 mL) and water (0.52 mL), and the suspension was stirred at 100° C. for 6 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated, purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.0087 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by NH silica gel column chromatography (ethyl acetate/hexane)
  8. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f5599760591c47e498135494c97a990e
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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