Benzylamine → HCID 69156557, compound

HRID 750151Notes

Reaction equation

HRID 750151 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:47][O:48][C:49]([C:51]1[N:52]([CH2:69][C:70]2[CH:78]=[CH:77][C:73]3[O:74][CH2:75][O:76][C:72]=3[CH:71]=2)[C:53](=[O:68])[C:54]2[C:59]([C:60]=1[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[CH:58][C:57](Br)=[CH:56][CH:55]=2)=[O:50].[CH2:79]([NH2:86])[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:47][O:48][C:49]([C:51]1[N:52]([CH2:69][C:70]2[CH:78]=[CH:77][C:73]3[O:74][CH2:75][O:76][C:72]=3[CH:71]=2)[C:53](=[O:68])[C:54]2[C:59]([C:60]=1[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[CH:58][C:57]([NH:86][CH2:79][C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)=[CH:56][CH:55]=2)=[O:50]

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 634876Binap, (A+-)-HCID 10239063HCID 10239063, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 69156557HCID 69156557, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Palladium(II) acetate (15 mg) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (130 mg) were added to toluene (20 ml) at room temperature, and the mixture was stirred for 5 min. under a nitrogen atmosphere. To the reaction mixture were added 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (1.0 g) and benzylamine (0.33 ml) at room temperature, and the mixture was stirred for 10 min under a nitrogen atmosphere. To the reaction mixture was further added sodium tert-butoxide (270 mg) at room temperature, and heated under reflux under a nitrogen atmosphere for 4 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, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) to give the title compound (1 g).

Workup

  1. stirringthe mixture was stirred for 10 min under a nitrogen atmosphere
  2. customat room temperature
  3. temperatureheated
  4. temperatureunder reflux under a nitrogen atmosphere for 4 hrs
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-3fcffca1192d402d95b6ac8646e4efaa
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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