Toluene → HCID 69156849, compound

HRID 750147Notes

Reaction equation

HRID 750147 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(C)C=CC=CC=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(O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:10][CH:9]=2)=[O:4]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium Carbonate2×HCID 66827Phenylboronic Acid2×HCID 10239063HCID 10239063, compound

Product 1

HCID 69156849HCID 69156849, compoundYield 87.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), phenylboronic acid (100 mg), tetrakis(triphenylphosphine)palladium(0) (35 mg), toluene (6 ml), ethanol (0.8 ml) and 2M aqueous sodium carbonate solution (0.8 ml) was heated under reflux under a nitrogen atmosphere for 6 hrs. To the reaction mixture were further added dihydroxyphenylborane (100 mg), tetrakis(triphenylphosphine)palladium(0) (35 mg), ethanol (0.8 ml) and 2M aqueous sodium carbonate solution (0.8 ml), and the mixture was heated under reflux for 6 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and recrystallized (ethyl acetate-hexane) to give the title compound (260 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under a nitrogen atmosphere for 6 hrs
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 6 hrs
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialThe solvent was dried over anhydrous sodium sulfate
  8. concentrationwas concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1)
  10. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-399c096d07734faeb0bc84099524f00a
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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