4-Bromoisoquinoline → HCID 10942859, compound

HRID 970410Notes

Reaction equation

HRID 970410 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-470c861d22dc4288b8c9e2468e3618c1
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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