Ethyl Acetate → HCID 22503440, compound

HRID 1814560Notes

Reaction equation

HRID 1814560 reaction equation
C(OCC[C:7]1[CH:12]=[CH:11][C:10]([Sn](CCCC)(CCCC)CCCC)=[C:9]([F:26])[CH:8]=1)(=O)C.Br[C:28]1[N:29]=[C:30]([N:38]2[CH2:43][CH2:42][N:41]([CH2:44][CH3:45])[CH2:40][CH2:39]2)[C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2.[C:46]([O:49][CH2:50][CH3:51])(=[O:48])[CH3:47]>C1(C)C(C)=CC=CC=1.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>[CH2:44]([N:41]1[CH2:42][CH2:43][N:38]([C:30]2[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:37]=[C:28]([C:7]3[CH:12]=[CH:11][C:10]([CH2:51][CH2:50][O:49][C:46](=[O:48])[CH3:47])=[C:9]([F:26])[CH:8]=3)[N:29]=2)[CH2:39][CH2:40]1)[CH3:45]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 22503492HCID 22503492, compound

Product 1

HCID 22503440HCID 22503440, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

2-(3-Fluoro-4-tributylstannylphenyl)ethyl acetate (2.77 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (1.19 g) were heated under reflux overnight in the presence of tetrakistriphenylphosphinepalladium(0) (0.17 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. The 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 organic layer 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 (1.44 g) of 1-(4-ethylpiperazin-1-yl)-3-[3-fluoro-4-(2-acetoxyethyl)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 aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer 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-aef42da6c78347c0aecf83e3c5f74c69
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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