2,2,2-Trifluoroethyl trifluoromethanesulfonate → 5-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

HRID 627713Notes

Reaction equation

HRID 627713 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].FC(F)(F)S(O[CH2:18][C:19]([F:22])([F:21])[F:20])(=O)=O>>[F:20][C:19]([F:22])([F:21])[CH2:18][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:2])=[O:4])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

HCID 574758545-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acidYield 83.1%

Procedure

Analogous to the preparation of intermediate 49, 5-hydroxy-2-pyridinecarboxylic acid methyl ester (0.253 mL, 2.122 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.739 mL, 3.18 mmol) were combined to afford the title compound (390 mg, 1.764 mmol, 83%) as a white solid. MS m/z=222.1 (M+H).

Sources & evidence

ORD record
ord-361a5d79854c436185e00503cb99a6c2
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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