Tributylvinyltin → HCID 68852686, compound

HRID 1785244Notes

Reaction equation

HRID 1785244 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH:13]([C:15]2[S:16][C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:18][C:19]=2I)[CH3:14])=[CH:8][C:7]=1[CH3:31].[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH:13]([C:15]2[S:16][C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:18][C:19]=2[CH:33]=[CH2:34])[CH3:14])=[CH:8][C:7]=1[CH3:31]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 68855304HCID 68855304, compound

Product 1

HCID 68852686HCID 68852686, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The solution of 3-(4-{1-[3-Iodo-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethylsulfanyl}-2-methyl-phenyl)-propionic acid methyl ester (0.195 g, 0.348 mmole) and tributyl(vinyl)tin (0.331 g, 1.04 mmole) in toluene (3 mL) is bubbled with nitrogen gas for 10 minutes. To it is added tetrakis(triphenylphosphine)palladium(0) (0.20 g). The reaction is heated under 80° C. overnight. The mixture is concentrated, loaded to a silica gel column, eluted with ethyl acetate in hexane (0-15%) and concentrated to provide the titled compound as colorless oil.

Workup

  1. concentrationThe mixture is concentrated
  2. washeluted with ethyl acetate in hexane (0-15%)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0fe04c369f834c55bf75cf7cae10a5ea
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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