Pyridine → HCID 86666250, compound

HRID 533404Notes

Reaction equation

HRID 533404 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[CH:20]=[CH:19][N:18]=1.N1C=CC=CC=1.ClCCl>O>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[CH:20]=[CH:19][N:18]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 178497278HCID 178497278, compound

Product 1

HCID 86666250HCID 86666250, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoromethanesulfonic anhydride (2.1 g) was added to a mixture of methyl 1-hydroxyisoquinoline-7-carboxylate (1.3 g), pyridine (587 mg), and dichloromethane (40 mL), followed by stirring at room temperature for 18 hours. The reaction mixture was diluted with water, extracted with chloroform, and the organic layer was concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (chloroform/methanol) to obtain methyl 1-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-7-carboxylate (1.9 g).

Workup

  1. extractionextracted with chloroform
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe resulting residue was purified under silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a33036958182427abe7ccb10c39c8d5f
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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