3-Ethynylbenzoic acid methyl ester → HCID 67703751, compound

HRID 55266Notes

Reaction equation

HRID 55266 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=[C:8](I)[N:7]=1.[CH3:29][O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[CH:39])[CH:33]=1>>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=[C:8]([C:39]#[C:38][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([O:30][CH3:29])=[O:40])[CH:33]=2)[N:7]=1

Participants

3

Reactant 2

HCID 112751593-Ethynylbenzoic acid methyl esterHCID 867507633-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 67703751HCID 67703751, compoundYield 79.2%

Procedure

Under the conditions of example 5 A, 1 g of 3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is reacted with 320 mg of 3-ethinylbenzoic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-15% ethyl acetate. 835 mg of 3-{6-[2-(3-methoxycarbonylphenyl)-ethinyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-15% ethyl acetate

Sources & evidence

ORD record
ord-134af14b902046eb9036ffa2c7d92eef
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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