Toluene → 3-[(E)-2-phenylvinyl][1,4]benzodioxino[2,3-c]pyridazine

HRID 1503203Notes

Reaction equation

HRID 1503203 reaction equation
C1(C)C=CC=CC=1.Cl[C:9]1[N:14]=[N:13][C:12]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[O:18][C:11]=2[CH:10]=1.[C:23]1(/[CH:29]=[CH:30]/B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[C:23]1(/[CH:29]=[CH:30]/[C:9]2[N:14]=[N:13][C:12]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[O:18][C:11]=3[CH:10]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 5702628Styrylboronic acidHCID 122134663-Chlorobenzo[5,6][1,4]dioxino[2,3-c]pyridazine

Product 1

HCID 1176908813-[(E)-2-phenylvinyl][1,4]benzodioxino[2,3-c]pyridazineYield 49.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Toluene (10 ml) was added to 3-chloro[1,4]benzodioxino[2,3-c]pyridazine (600 mg), and (E)-2-phenylvinylboronic acid (480 mg), tetrakis(triphenylphosphine)palladium (315 mg) and 2M aqueous sodium carbonate solution (1.6 mL) were added at room temperature. The reaction mixture was stirred at 120° C. for 14 hr. Water was added and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The obtained residue was washed with a mixed solvent of hexane and ethyl acetate and filtered. The obtained solid was dried under reduced pressure to give 3-[(E)-2-phenylvinyl][1,4]benzodioxino[2,3-c]pyridazine (386 mg).

Workup

  1. additionwere added at room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. washThe obtained residue was washed with a mixed solvent of hexane and ethyl acetate
  7. filtrationfiltered
  8. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-c9bbc95376154e2f9170570918ae598e
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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