4-Bromoisoquinoline → HCID 10942859, compound

HRID 2270095Notes

Reaction equation

HRID 2270095 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.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14]>C1(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>[CH2:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1)[CH:13]=[CH2:12]

Participants

5

Reactant 2

HCID 737434-BromoisoquinolineHCID 90628Allyltributylstannane

Product 1

HCID 10942859HCID 10942859, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-bromoisoquinoline (2.0 g) in 70 mL of toluene was added allyl tributyl stannane (3.28 mL) and Pd(PPh3)4 (1.10 g). The resulting solution was heated at reflux for 12 hours and then cooled to room temperature. The solution was concentrated in vacuo, dissolved in ether and washed successively with an aqueous solution of trithiocyanuric acid trisodium salt, water and brine. The organic layer was then dried over magnesium sulfate, filtered, concentrated in vacuo, and purified using flash chromatography (silica, 0-30% EtOAc/hexanes) to provide 0.965 g of 4-(2-propenyl)-isoquinoline. Mass spectrum [NH3/CI], (M+H)+=170.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 12 hours
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutiondissolved in ether
  5. washwashed successively with an aqueous solution of trithiocyanuric acid trisodium salt, water and brine
  6. dry with materialThe organic layer was then dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified

Sources & evidence

ORD record
ord-1620ac7e059c43468bb092b65bb0e578
Source dataset
uspto-grants-2001_12
Patent number
US06331545B1

Reaction notes

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