Pyridine → 2-Pyridyl Trifluoromethanesulfonate

HRID 1713012Notes

Reaction equation

HRID 1713012 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10]>C(Cl)Cl>[O:12]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 39476262-Pyridyl TrifluoromethanesulfonateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to GP 2, reaction of 4.19 g Intermediate 2 (14.8 mmol, 1 eq.), 1.79 mL dry pyridine (22.2 mmol, 1.5 eq.), 3.73 ml trifluoromethanesulfonic acid anhydride (22.2 mmol, 1.5 eq.) in 110 mL DCM yielded 5.6 g 2-pyridyl triflate (13.5 mmol, 91% yield).

Sources & evidence

ORD record
ord-c41f21e260d04abdaa5b213ffabe1435
Source dataset
uspto-grants-2010_09
Patent number
US07795264B2

Reaction notes

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