Water → HCID 11417829, compound

HRID 457258Notes

Reaction equation

HRID 457258 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:33])/[C:15](/[Sn](CCCC)(CCCC)CCCC)=[CH:16]\[CH:17]([CH3:19])[CH3:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:34][C:35]1[CH:40]=[CH:39][C:38](I)=[CH:37][CH:36]=1.O>CN(C)C=O.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.[Cu]I>[Cl:34][C:35]1[CH:40]=[CH:39][C:38](/[C:15](=[CH:16]/[CH:17]([CH3:18])[CH3:19])/[C:14]([NH:13][CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:33])=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 962WaterHCID 125101-Chloro-4-iodobenzeneHCID 11365077HCID 11365077, compound

Product 1

HCID 11417829HCID 11417829, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 10 g (17.6 mmol) of (2E)-N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methyl-2-(tributylstannyl)-2-pentenamide (5) in 15 ml of dimethylformamide (DMF) was mixed with 4.2 g (17.7 mmol) of 4-chloroiodobenzene, 0.5 g of Pd(PPh3)4 and 0.5 g of copper(I) iodide. After stirring for approximately 14 hours at 20 to 25° C., the reaction solution was poured into water and extracted with MTBE. The organic phases were washed with water, dried and freed from the solvent. After chromatographing on silica gel (cyclohexane:MTBE [7:1 to 1:1]), 5.8 g of the title compound were obtained.

Workup

  1. extractionextracted with MTBE
  2. washThe organic phases were washed with water
  3. customdried

Sources & evidence

ORD record
ord-600d856d8aaa428894f29e98eee0f2c9
Source dataset
uspto-grants-2007_03
Patent number
US07186861B2

Reaction notes

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