Toluene → HCID 69671278, compound

HRID 1191659Notes

Reaction equation

HRID 1191659 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:10]=[C:9]([O:11][CH:12]([F:14])[F:13])[CH:8]=[CH:7][C:5]=1[NH2:6].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[F:13][CH:12]([F:14])[O:11][C:9]1[CH:10]=[C:4]2[C:5](=[CH:7][CH:8]=1)[NH:6][C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:3]2

Participants

8

Reactant 4

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 86665745HCID 86665745, compound

Product 1

HCID 69671278HCID 69671278, compoundYield 72.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-(2,2-dibromovinyl)-4-difluoromethoxyaniline (166 mg), phenylboronic acid (88.5 mg) and potassium phosphate monohydrate (557 mg) was added a mixture of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (11.9 mg), palladium (II) acetate (3.3 mg) and toluene (2.4 mL) at room temperature, and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and then filtered through celite (registered trademark). The filtrate was washed with saturated saline-water (2/1), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (91.2 mg).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through celite (registered trademark)
  4. washThe filtrate was washed with saturated saline-water (2/1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f2f4e1214c014bbb825359302692de7f
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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