Tributylvinyltin → HCID 68808761, compound

HRID 2217855Notes

Reaction equation

HRID 2217855 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:22])[C:8]=2[NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:3]=1.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[Cl:22][C:7]1[C:8]([NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH:23]=[CH2:24])[CH:11]=[CH:10]2

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide

Product 1

HCID 68808761HCID 68808761, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (2 g) in dimethylformamide (6 mL) was added tributyl(vinyl)tin (3.63 g), 2,6-di-tert-butyl-4-methylphenol (50 mg) and dichlorobis(triphenylphosphine)palladium (0.25 g). The reaction was heated at 80° C. under nitrogen for 6 hours and then cooled to room temperature. The mixture was filtered through diatomaceous earth and poured into water and dichloromethane. The organic layer was separated and the aqueous was further extracted with dichloromethane. The combined organic layers were dried, filtered and evaporated. Purification (SiO2, methanol:dichloromethane 5:95 as eluant) gave the sub-titled compound (1.2 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. additionpoured into water and dichloromethane
  4. customThe organic layer was separated
  5. extractionthe aqueous was further extracted with dichloromethane
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. customevaporated
  9. customPurification (SiO2, methanol:dichloromethane 5:95 as eluant)

Sources & evidence

ORD record
ord-4b11e245835b411d84a506285fe1d482
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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