Tributylvinyltin → HCID 69743649, compound

HRID 1760368Notes

Reaction equation

HRID 1760368 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2].[CH:30]([Sn](CCCC)(CCCC)CCCC)=[CH2:31]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:30]=[CH2:31])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 12133937HCID 12133937, compound

Product 1

HCID 69743649HCID 69743649, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[6-(4-bromo-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (5.8 g, 12.2 mmol), vinyltributyltin (3.9 mL, 12.3 mmol), tetrakistriphenylphosphine palladium (0) (0.60 g, 0.52 mmol) and 24 mL of toluene was heated to reflux for 1 hour. After cooling to room temperature, the mixture was concentrated in vacuo and purified by silica gel chromatography (Flash 40, 20%-50% ethyl acetate-hexanes), affording 4.8 g of 1-[6-(4-Vinyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester as a colorless syrup.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by silica gel chromatography (Flash 40, 20%-50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-508664a0e18c4216966ef3dd6e41f5cb
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

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