Methyl 5-ethynylnicotinate → 3-{6-[2-(5-methoxycarbonyl-3-pyridyl)-ethinyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[CH:7]=[N:6][CH:5]=1.[CH3:13][O:14][C:15](=[O:40])[CH2:16][CH2:17][C:18]1[C:23]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:22][CH:21]=[C:20](I)[N:19]=1>>[CH3:13][O:14][C:15](=[O:40])[CH2:16][CH2:17][C:18]1[C:23]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]/[C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)=[CH:22][CH:21]=[C:20]([C:11]#[C:10][C:8]2[CH:7]=[N:6][CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:9]=2)[N:19]=1Participants
3
Reactant 2
Product 1
Procedure
Under the conditions of example 5A, 184 mg of the crude 5-ethinylnicotinic acid methyl ester is reacted with 500 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/0-30% ethyl acetate and for complete purification subjected to high-pressure liquid chromatography on reversed-phase silica gel (Nova-Pak HR C18) with acetonitrile/water=75/25. 15 mg of 3-{6-[2-(5-methoxycarbonyl-3-pyridyl)-ethinyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as oil.
Workup
- customthe crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate and for complete purification
Sources & evidence
- ORD record
- ord-e854e14f2c4546758bda00bbf35282c4
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624943
Reaction notes
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