Trifluoromethanesulfonic anhydride → HCID 18675884, compound

HRID 2052980Notes

Reaction equation

HRID 2052980 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 thereto dropwise. The mixture is stirred at 0° C. for 1 hour and then at ambient temperature for 2 hours. It is poured into a water/ice mixture and extracted with ethyl acetate, the organic phase is dried and the solvent is evaporated under reduced pressure. The crude product is purified by chromatography on a column of silica gel, elution being carried out with a cyclohexane/ethyl acetate=7/3 mixture. 7-Hydroxyisoquinoline trifluoromethanesulfonate is obtained in the form of an oil. 1.65 g of this product are mixed under argon 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. The mixture is heated at 80° C. for 36 hours. It 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 under reduced pressure. The residue is purified by chromatography on a column of silica gel, elution being carried out with an ethyl acetate/methanol=9/1 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% sulfuric acid. The mixture is heated at 60° C. for 4.5 hours and is poured into ice, a saturated aqueous NaHCO3 solution is added thereto and extraction is carried out with ethyl acetate. The organic phase is dried and the solvent is evaporated under reduced pressure. The title compound is obtained.

Workup

  1. waitat ambient temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is dried
  4. customthe solvent is evaporated under reduced pressure
  5. customThe crude product is purified by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-33c151a044b44e259ba695e613f3684d
Source dataset
uspto-grants-2008_02
Patent number
US07326720B2

Reaction notes

Loading…