Piconol → (RS)-[2,6-difluoro-4-(pyridin-2-ylmethoxy)-phenyl]-ethoxy-acetic acid ethyl ester

HRID 1247435Notes

Reaction equation

HRID 1247435 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2].O[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

3

Reactant 2

HCID 11474PiconolHCID 69290842(RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester

Product 1

HCID 69291981(RS)-[2,6-difluoro-4-(pyridin-2-ylmethoxy)-phenyl]-ethoxy-acetic acid ethyl ester

Procedure

In analogy to example 22.1 (RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester (example L6) was reacted with 2-(hydroxymethyl)pyridine to give (RS)-[2,6-difluoro-4-(pyridin-2-ylmethoxy)-phenyl]-ethoxy-acetic acid ethyl ester as a yellow semisolid. This material was hydrolysed in analogy to example 101.3 to give (RS)-[2,6-difluoro-4-(pyridin-2-ylmethoxy)-phenyl]-ethoxy-acetic acid. White solid. MS 324.1 ([M+H]+)

Sources & evidence

ORD record
ord-70d51dc71daf486a8a74d8f32a479546
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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