Triethylamine → Isoquinolin-3-yl trifluoromethanesulfonate

HRID 252125Notes

Reaction equation

HRID 252125 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].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18](O)[N:17]=1.C(N(CC)CC)C>ClCCl>[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178515325HCID 178515325, compound

Product 1

HCID 11231236Isoquinolin-3-yl trifluoromethanesulfonateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoromethanesulfonic anhydride (383 μL, 2.3 mmol) dropwise to a suspension of isoquinolin-3-ol (274 mg, 1.89 mmol) and triethylamine (524 μL, 3.8 mmol) in dichloromethane (12 mL). Stir for 40 min, then load onto a silica column and elute with dichloromethane to give trifluoro-methanesulfonic acid isoquinolin-3-yl ester as a white solid (505 mg, 97%).

Workup

  1. washload onto a silica column and elute with dichloromethane

Sources & evidence

ORD record
ord-5c2b9af9480b45ec9f2f2fcc101bd8d3
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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