Tri(butyl)vinyltin → HCID 59410169, compound

HRID 85224Notes

Reaction equation

HRID 85224 reaction equation
Br[C:2]1[C:3](=[O:19])[N:4]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=2[CH3:18])[CH:5]=[CH:6][CH:7]=1.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC>O1CCOCC1.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>[CH3:18][C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[C:13]([CH3:14])[C:8]=1[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:20]=[CH2:21])[C:3]1=[O:19]

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 594102073-Bromo-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one

Product 1

HCID 59410169HCID 59410169, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

132 g (408 mmol) of the compound from Example 59A (alternative synthesis) are dissolved in 1.27 l of anhydrous dioxane, 136 g (428 mmol) of tributylvinyltin and 9.44 g (8.17 mmol) of tetrakis(triphenylphosphine)palladium are added and the mixture is stirred at 100° C. for 4 h. The mixture is allowed to cool and filtered through kieselguhr. The mixture is concentrated to dryness under reduced pressure. The residue is dissolved in dichloromethane and purified by chromatography on silica gel (petroleum ether/ethyl acetate 9:1, then 8:2, then 7:3). The product-containing fractions are combined, the solvents are removed and the residue is triturated with petroleum ether/diethyl ether (10:1). This gives 83 g (75% of theory) of the desired product.

Workup

  1. temperatureto cool
  2. filtrationfiltered through kieselguhr
  3. concentrationThe mixture is concentrated to dryness under reduced pressure
  4. dissolutionThe residue is dissolved in dichloromethane
  5. custompurified by chromatography on silica gel (petroleum ether/ethyl acetate 9:1
  6. customthe solvents are removed
  7. customthe residue is triturated with petroleum ether/diethyl ether (10:1)

Sources & evidence

ORD record
ord-bcf33cd5bdb04c018e91b58286049711
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

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