Potassium Carbonate → 5-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester

HRID 1941815Notes

Reaction equation

HRID 1941815 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:32])([CH:29]([F:31])[F:30])[CH2:20]OS(C(F)(F)F)(=O)=O>CC(C)=O.C(OCC)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][C:19]([F:32])([F:18])[CH:29]([F:31])[F:30])=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 37924752,2,3,3-Tetrafluoropropyl trifluoromethanesulfonateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

HCID 574758745-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-hydroxy-pyridine-2-carboxylic acid methyl ester (2.0 g, 13.1 mmol) in acetone (40 ml) was treated with potassium carbonate (5.415 g, 39.2 mmol) and trifluoro-methanesulphonic acid 2,2,3,3-tetrafluoropropyl ester. After 4 hours stirring at room temperature the suspension was diluted with diethylether. After filtration the solution was evaporated and the yellow solid purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 30:70 as the eluent. The 5-(2,2,3,3-tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester was obtained as a light yellow solid (3.49 g, 76% of theory). MS (ISP): m/z=468.1 [M+H]+. b) 5-(2,2,3,3-Tetrafluoro-propoxy)-pyridine-2-carboxylic acid In a manner analogous to that described in example 29b), the hydrolysis of the 5-(2,2,3,3-tetrafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester with lithium hydroxide yielded the title compound as a light yellow solid (yield 94% of theory). MS (ISP): m/z=253 [M]+.

Workup

  1. filtrationAfter filtration the solution
  2. customwas evaporated
  3. customthe yellow solid purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 30:70 as the eluent

Sources & evidence

ORD record
ord-2b072842f0ac414a84bc6fb95b231726
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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