Propargyl alcohol → 3-(8-Isoquinolinyl)-2-propyn-1-ol

HRID 1110479Notes

Reaction equation

HRID 1110479 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[C:14]#[C:13][CH2:12][OH:15])[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 98591348-Bromoisoquinoline

Product 1

HCID 143474813-(8-Isoquinolinyl)-2-propyn-1-ol

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In an inert atmosphere, 0.068 g of bis(triphenylphosphine)palladium dichloride and 0.013 g of cuprous iodide was added with stirring to a deoxygenated solution of 1 g of 8-bromoisoquinoline, 0.56 mL of propargyl alcohol and 2 mL of triethylamine in 25 mL of dichloromethane. The mixture was stirred at room temperature for 2 hours and then at reflux for 20 hours. The cooled reaction was filtered and the filtrate was concentrated in vacuo. The residual oil was purified by HPLC (ethyl acetate-toluene; 2:3) to yield 0.4 g of 3-(8-isoquinolinyl)-2-propyn-1-ol, mp 138°-139° C.

Workup

  1. temperatureat reflux for 20 hours
  2. customThe cooled reaction
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residual oil was purified by HPLC (ethyl acetate-toluene; 2:3)

Sources & evidence

ORD record
ord-2426ef2bb1874a6fbb0c68c654cf6782
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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