(Z)-1-Ethoxy-2-(tributylstannyl)ethene → 6-acetyl-3-[6-(4-methoxyphenyl-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

HRID 55264

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[NH:7][C:8](I)([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:9]=[CH:10][CH:11]=1.[CH2:29]([O:31]C=C[Sn](CCCC)(CCCC)CCCC)[CH3:30]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[NH:7][C:8]([C:29](=[O:31])[CH3:30])([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:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 495 mg of 3-{6-iodo-3-[6-(4-methoxyphenyl-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester and 397 mg of ethoxyvinyltributyltin in 2 ml of toluene is mixed with 30 mg of bis-triphenylphosphine-palladium(II) chloride and heated for six hours with stirring to 110° C. The reaction mixture is filtered on diatomaceous earth, the filter residue is washed with diethyl ether, the filtrate is mixed with 1.5 ml of 2n hydrochloric acid and stirred for 4 hours at room temperature. The organic phase is separated, dried with sodium sulfate and concentrated by evaporation. 95 mg of 3-{6-acetyl-3-[6-(4-methoxyphenyl-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Workup

temperatureheated for six hours
filtrationThe reaction mixture is filtered on diatomaceous earth
washthe filter residue is washed with diethyl ether
additionthe filtrate is mixed with 1.5 ml of 2n hydrochloric acid
stirringstirred for 4 hours at room temperature
customThe organic phase is separated
dry with materialdried with sodium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-5374a5b7c4d54206b10cb491f614f631
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624943

Linked notes

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