Tri(butyl)vinyltin → HCID 59410169, compound

HRID 452242Notes

Reaction equation

HRID 452242 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

2.00 g (6.19 mmol) of the compound from Example 51A are dissolved in 31 ml of anhydrous dioxane, and 2.36 g (7.42 mmol) of tributylvinyltin and 143 mg (0.124 mmol) of tetrakis(triphenylphosphine)palladium are added and the mixture is stirred at 100° C. for 5 h. The mixture is allowed to cool and filtered through kieselguhr. The filter cake is washed three times with ethyl acetate, and the combined filtrates are concentrated to dryness under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1). This gives 846 mg (51% of theory) of the desired product.

Workup

  1. temperatureto cool
  2. filtrationfiltered through kieselguhr
  3. washThe filter cake is washed three times with ethyl acetate
  4. concentrationthe combined filtrates are concentrated to dryness under reduced pressure
  5. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-4d5f354978f142a2a818839414b468c7
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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