2-Fluoroethyl bromide → 5-(2-Fluoroethoxy)pyridine-2-carboxylic acid

HRID 1929513Notes

Reaction equation

HRID 1929513 reaction equation
C1(COC2C=CC(C(O)=O)=NC=2)CC1.COC(C1C=CC(O)=CN=1)=O.BrCCF.C[O:31][C:32]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][F:43])=[CH:36][N:35]=1)=[O:33]>>[F:43][CH2:42][CH2:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]([OH:33])=[O:31])=[N:35][CH:36]=1

Participants

5

Reactant 4

HCID 129822-Fluoroethyl bromideHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 666918955-(Cyclopropylmethoxy)pyridine-2-carboxylic acidHCID 866512285-(2-Fluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 790070915-(2-Fluoroethoxy)pyridine-2-carboxylic acid

Procedure

The 5-(2-fluoro-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 1-bromo-2-fluoroethane and hydrolysis of the 5-(2-fluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester yielded the 5-(2-fluoro-ethoxy)-pyridine-2-carboxylic acid as a white solid. Mass (calculated) C8H8FNO3 [185.153]; (found) [M+H]+=186.

Workup

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

Sources & evidence

ORD record
ord-7d0deb1a45dd4575a9fb393e3efe4fd4
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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