4-Ethynyl-benzeneacetic acid methyl ester → 3-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

HRID 55298Notes

Reaction equation

HRID 55298 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][CH:6]=1.[CH3:14][O:15][C:16](=[O:27])[CH2:17][CH2:18][C:19]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21](I)[N:20]=1>>[CH3:14][O:15][C:16](=[O:27])[CH2:17][CH2:18][C:19]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:13])=[CH:10][CH:9]=2)[N:20]=1

Participants

3

Reactant 2

HCID 539703584-Ethynyl-benzeneacetic acid methyl esterHCID 544750193-(3-Hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester

Product 1

HCID 677037393-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl esterYield 39.6%

Procedure

Under the conditions of example 5 A, 5 g of the crude 4-ethinylphenylacetic acid methyl ester is reacted with 7.9 g of 3-(3-hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-50% ethyl acetate. 3.6 g of 3-{3-hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester of melting point 122°-125° C. is obtained.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-50% ethyl acetate

Sources & evidence

ORD record
ord-c87c10f82a4f4be9a3c79877c903a68a
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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