Hydrochloric Acid → HCID 68957320, compound

HRID 2191839Notes

Reaction equation

HRID 2191839 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[NH2:46][C:47]1[CH:59]=[C:58]([CH2:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH:57]=[CH:56][C:48]=1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([NH:46][C:47]2[CH:59]=[C:58]([CH2:60][CH2:61][C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)[CH:57]=[CH:56][C:48]=2[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[CH:3][N:4]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 737434-BromoisoquinolineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 68957320HCID 68957320, compoundYield 40.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To toluene 1.0 mL solution of 4-bromoisoquinoline 0.12 g were added 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg, tert-butyl 2-amino-4-phenethylbenzoate 59 mg, cesium carbonate 0.13 g, palladium acetate 0.90 mg and tris(dibenzylideneacetone)dipalladium(0) 3.7 mg at room temperature, and it was heated and refluxed for 7 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution sequentially, and the solvent was removed under reduced pressure. Ethyl acetate and hexane were added to the obtained residue, and solid matter was filtrated to give tert-butyl 2-((isoquinolin-4-yl)amino)-4-phenethylbenzoate 34 mg of a yellow solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 7 hours
  3. customThe organic layer was separated
  4. washafter washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution sequentially
  5. customthe solvent was removed under reduced pressure
  6. additionEthyl acetate and hexane were added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-1118cad789fc42df9ef96d4d59487760
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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