N-(3-ethynylphenyl)-1,1,1-trifluoromethanesulfonamide → 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(3-trifluoromethanesulfonamidophenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

HRID 55309Notes

Reaction equation

HRID 55309 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH3:17][O:18][C:19](=[O:44])[CH2:20][CH2:21][C:22]1[C:27]([O:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)=[CH:26][CH:25]=[C:24](I)[N:23]=1>>[CH3:17][O:18][C:19](=[O:44])[CH2:20][CH2:21][C:22]1[C:27]([O:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]/[C:35]2[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=2)=[CH:26][CH:25]=[C:24]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][S:10]([C:13]([F:16])([F:14])[F:15])(=[O:12])=[O:11])[CH:4]=2)[N:23]=1

Participants

3

Reactant 2

HCID 19957419N-(3-ethynylphenyl)-1,1,1-trifluoromethanesulfonamideHCID 867507633-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 677038723-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(3-trifluoromethanesulfonamidophenyl)-ethinyl]-2-pyridyl}-propionic acid methyl esterYield 32.7%

Procedure

Under the conditions of example 5 A, 370 mg of crude N-(3-ethinylphenyl)-1,1,1-trifluoromethanesulfonamide is reacted with 735 mg of 3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-20% ethyl acetate. 299 mg of 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(3-trifluoromethanesulfonamidophenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Workup

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

Sources & evidence

ORD record
ord-92fce624ee944e138732a081936d55d8
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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