Pyridine → 2-Pyridyl Trifluoromethanesulfonate

HRID 2261005Notes

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].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[O:6]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=1)[S:3]([C:2]([F:15])([F:14])[F:1])(=[O:4])=[O:5]

Participants

Reactant 2

HCID 1049Pyridine

HCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 39476262-Pyridyl TrifluoromethanesulfonateYield 68%

Procedure

In a modification to GP 2, reaction of 1.5 g Intermediate 1.4 (5.3 mmol, 1 eq.), and 2.69 ml trifluoromethanesulfonic acid anhydride (16 mmol, 3 eq.) in pure pyridine yielded 1.49 g 2-pyridyl triflate (3.6 mmol, 68% yield).

Sources & evidence

ORD record: ord-b2ba2d2087eb4544ba79619ca7b266e4
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846928B2

Reaction notes

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