3-Ethynylbenzoic acid methyl ester → 3-{3-Hydroxy-6-[2-(3-methoxycarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

HRID 55315Notes

Reaction equation

HRID 55315 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8](I)[N:7]=1.[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=1>>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]([C:25]#[C:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([O:16][CH3:15])=[O:26])[CH:19]=2)[N:7]=1

Participants

3

Reactant 2

HCID 112751593-Ethynylbenzoic acid methyl esterHCID 544750193-(3-Hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester

Product 1

HCID 544923413-{3-Hydroxy-6-[2-(3-methoxycarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl esterYield 46.2%

Procedure

Under the conditions of example 5A, 9.2 g of 3-(3-hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester is reacted with 4.8 g of 3-ethinylbenzoic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-20% ethyl acetate. 4.7 g of 3-{3-hydroxy-6-[2-(3-methoxycarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester of melting point 125°-127° C. is obtained.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-20% ethyl acetate

Sources & evidence

ORD record
ord-544f5b679e534578886630149d855777
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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