(Z)-1-Ethoxy-2-(tributylstannyl)ethene → HCID 59164443, compound

HRID 906503Notes

Reaction equation

HRID 906503 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8](I)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17].C([Sn](CCCC)(CCCC)[CH:25]=[CH:26][O:27][CH2:28][CH3:29])CCC>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:26]([O:27][CH2:28][CH3:29])=[CH2:25])[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 591644332-Acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 59164443HCID 59164443, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (17.8 g, 46.1 mmol), tetrakis-(triphenylphosphine)-palladium (2.67 g, 2.30 mmol), and tributyl-(ethoxyvinyl)-tin (25.0 g, 69.2 mmol) in dioxane (100 mL) was heated to 110° C. for 20 h under nitrogen. The mixture was allowed to cool to r.t., and then filtered. The filtrate was concentrated in vacuo and the crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 3:1) to give crude 2-acetylamino-5-(1-ethoxy-vinyl)-4-trifluoromethyl-benzoic acid methyl ester as an orange solid, m.p. 65-73° C., ESI-MS: m/z 332 [M+H]+. This crude product was used without further purification in the next step.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 3:1)

Sources & evidence

ORD record
ord-f80048e7d4c340728645c7445d072258
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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