Triethylamine → 4-(Isoquinolin-4-yl)but-3-yn-1-ol

HRID 1651107Notes

Reaction equation

HRID 1651107 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]([OH:16])[CH2:13][C:14]#[CH:15].C(N(CC)CC)C>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:15]#[C:14][CH2:13][CH2:12][OH:16])=[CH:3][N:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 737434-Bromoisoquinoline

Product 1

HCID 106317934-(Isoquinolin-4-yl)but-3-yn-1-olYield 71.7%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

In an inert atmosphere, 0.268 g of bis(triphenylphosphine) palladium dichloride and 0.072 g of cuprous iodide was added with stirring to a deoxygenated solution of 5 g of 4-bromoisoquinoline, 3.02 g of 3-butyn-1-ol and 10 mL of triethylamine in 20 mL of dichloromethane. The reaction was stirred at room temperature for 1 hour and then at reflux for 18 hours. The cooled mixture was filtered and the filtrate was washed with water. The dried (Na2SO4) organic phase was concentrated in vacuo and the residual oil was purified by HPLC (ethyl acetate-toluene; 2:3) to yield 3.4 g of 4-(4-isoquinolinyl)-3-butyn-1-ol as an oil.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationThe cooled mixture was filtered
  3. washthe filtrate was washed with water
  4. dry with materialThe dried (Na2SO4) organic phase
  5. concentrationwas concentrated in vacuo
  6. customthe residual oil was purified by HPLC (ethyl acetate-toluene; 2:3)

Sources & evidence

ORD record
ord-fd6a620ba1cf4576b5e6729ab55891bd
Source dataset
uspto-grants-1990_05
Patent number
US04927826

Reaction notes

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