Toluene → HCID 67774811, compound

HRID 533399Notes

Reaction equation

HRID 533399 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[C:5]([C:16]2[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=2[F:24])=[N:4][CH:3]=1.[CH:25]1(P(C2CCCCC2)C2CCCCC2)CCCC[CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:24][C:17]1[CH:18]=[C:19]([F:23])[CH:20]=[C:21]([F:22])[C:16]=1[C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=2)[C:2]([CH:25]=[CH2:26])=[CH:3][N:4]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 67773046HCID 67773046, compound

Product 1

HCID 67774811HCID 67774811, compoundYield 326.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Under argon gas atmosphere, a mixture of methyl 4-bromo-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (292 mg), 2,4,6-trivinylboroxin-pyridine complex (89 mg), palladium acetate (19 mg), tricyclohexylphosphine (45 mg), tripotassium phosphate (280 mg), toluene (7 mL), and water (0.5 mL) was heated under stirring in an oil bath at 100° C. for 12 hours. The reaction mixture was returned to room temperature, diluted with water and ethyl acetate, and then the insoluble materials were separated by filtration. The filtrate was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 1-(2,4,6-trifluorophenyl)-4-vinylisoquinoline-7-carboxylate (180 mg).

Workup

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. customthe insoluble materials were separated by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-17e80644d087455d9ace426c966e527e
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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