Trifluoromethanesulfonic anhydride → HCID 18675884, compound

HRID 1635098Notes

Reaction equation

HRID 1635098 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[S:12]([O:19]S(C(F)(F)F)(=O)=O)([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13]>N1C=CC=CC=1>[F:16][C:15]([F:18])([F:17])[S:12]([OH:19])(=[O:14])=[O:13].[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 4597677-Isoquinolinol

Product 1

HCID 18675884HCID 18675884, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1.5 g (0.0103 mol) of 7-hydroxyisoquinoline and 5.3 ml of pyridine are cooled to 0° C. 1.86 ml of triflic anhydride are added dropwise thereto. The mixture is stirred for 1 hour at 0° C. and then for 2 hours at room temperature. The resulting mixture is poured into a water/ice mixture and extracted with ethyl acetate, the organic phase is dried and the solvent is evaporated off under reduced pressure. The crude product is purified by chromatography on a column of silica gel, eluting with a 7/3 cyclohexane/ethyl acetate mixture. 7-Hydroxyisoquinoline trifluoromethanesulphonate is obtained in the form of an oil. 1.65 g of this product are mixed with 27.5 ml of anhydrous dimethylformamide, 41 mg of palladium acetate, 1.65 ml of anhydrous triethylamine and 1.38 g of N,N-diethylethanolamine vinyl ether, under argon. This mixture is heated at 80° C. for 36 hours. The resulting mixture is poured into a water/ethyl acetate mixture, the two phases are separated, the organic phase is washed with water and dried, and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a 9/1 ethyl acetate/methanol mixture. 2-[2-(7-Isoquinolyl(ethenyl)oxy)]-N,N-diethyl-1-ethanamine is obtained. 1.5 g of this product are treated with 130 ml of water and 13 ml of 96% sulphuric acid. This mixture is heated for 4.5 hours at 60° C. and poured into ice, saturated aqueous NaHCO3 solution is added thereto and the mixture is extracted with ethyl acetate. The organic phase is dried and the solvent is evaporated off under reduced pressure. The title compound is obtained.

Workup

  1. waitfor 2 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is dried
  4. customthe solvent is evaporated off under reduced pressure
  5. customThe crude product is purified by chromatography on a column of silica gel
  6. washeluting with a 7/3 cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-4214cd734d5e4f1b91335c442d99bd94
Source dataset
uspto-grants-2003_01
Patent number
US06509351B1

Reaction notes

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