2,2-Difluoroethyl trifluoromethanesulfonate → 5-(2,2-Difluoro-ethoxy)-pyridine-2-carboxylic acid

HRID 1929514Notes

Reaction equation

HRID 1929514 reaction equation
C1(COC2C=CC(C(O)=O)=NC=2)CC1.COC(C1C=CC(O)=CN=1)=O.O(CC(F)F)S(C(F)(F)F)(=O)=O.C[O:39][C:40]([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH:50]([F:52])[F:51])=[CH:44][N:43]=1)=[O:41]>>[F:52][CH:50]([F:51])[CH2:49][O:48][C:45]1[CH:46]=[CH:47][C:42]([C:40]([OH:41])=[O:39])=[N:43][CH:44]=1

Participants

5

Reactant 4

HCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 578277635-(2,2-Difluoro-ethoxy)-pyridine-2-carboxylic acid methyl esterHCID 666918955-(Cyclopropylmethoxy)pyridine-2-carboxylic acid

Product 1

HCID 574758725-(2,2-Difluoro-ethoxy)-pyridine-2-carboxylic acid

Procedure

The 5-(2,2-difluoro-ethoxy)-pyridine-2-carboxylic acid was prepared in a reaction sequence analogous to that in example 60 for the preparation of the 5-cyclopropylmethoxy-pyridine-2-carboxylic acid: Alkylation of the 5-hydroxy-pyridine-2-carboxylic acid methyl ester with 2,2-difluoroethyl triflate and hydrolysis of the 5-(2,2-difluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester yielded the 5-(2,2-difluoro-ethoxy)-pyridine-2-carboxylic acid as an off-white solid. Mass (calculated) C8H7F2NO3 [203.143]; (found) [M+H]+=204.

Workup

  1. customThe 5-(2,2-difluoro-ethoxy)-pyridine-2-carboxylic acid was prepared in a reaction sequence analogous to that in example 60

Sources & evidence

ORD record
ord-b20be17620aa41edb662b2798196c68f
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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