1-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline → HCID 22503481, compound

HRID 1814567Notes

Reaction equation

HRID 1814567 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]([CH3:28])([C:9]1[CH:14]=[CH:13][C:12]([Sn](CCCC)(CCCC)CCCC)=[CH:11][CH:10]=1)[CH3:8])(=[O:3])[CH3:2].Br[C:30]1[N:31]=[C:32]([N:40]2[CH2:45][CH2:44][N:43]([CH2:46][CH3:47])[CH2:42][CH2:41]2)[C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C.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>[CH2:46]([N:43]1[CH2:42][CH2:41][N:40]([C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:39]=[C:30]([C:12]3[CH:11]=[CH:10][C:9]([C:7]([CH3:8])([CH3:28])[CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=3)[N:31]=2)[CH2:45][CH2:44]1)[CH3:47]

Participants

6

Reactant 2

HCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 22502821HCID 22502821, compound

Product 1

HCID 22503481HCID 22503481, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-3-(4-tributylstannylphenyl)butyl acetate (4.05 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (1.10 g) were heated under reflux overnight in the presence of tetrakistriphenylphosphinepalladium(0) (0.16 g) in xylene in nitrogen atmosphere. After cooling, the reaction solution was diluted with ethyl acetate and filtered. The filtrate was extracted with 2N hydrochloric acid, and the resulting aqueous layer was washed with ethyl acetate, adjusted to pH 10 with a 8N aqueous solution of sodium hydroxide, and then extracted with ethyl acetate. The extract was washed with a 10% aqueous solution of sodium carbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, to give a mixture (1.32 g) of 1-(4-ethylpiperazin-1-yl)-3-[4-(3-acetoxy-1,1-dimethylpropyl)phenyl]isoquinoline as a brown viscous oil and the starting material.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with 2N hydrochloric acid
  4. washthe resulting aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a 10% aqueous solution of sodium carbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-969693fcd39a4ec1a3254ed8ecdae743
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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