Tri(butyl)vinyltin → HCID 59410189, compound

HRID 85213Notes

Reaction equation

HRID 85213 reaction equation
Br[C:2]1[C:3](=[O:20])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[CH2:17][O:18][CH3:19])[CH:5]=[CH:6][CH:7]=1.[CH2:21](C([Sn])=C(CCCC)CCCC)[CH2:22]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>[CH3:19][O:18][CH2:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:21]=[CH2:22])[C:3]1=[O:20]

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 594101973-Bromo-1-[2-(methoxymethyl)-4-nitrophenyl]pyridin-2(1H)-one

Product 1

HCID 59410189HCID 59410189, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

94 g (277 mmol) of the compound from Example 28A are dissolved in 1.2 l of anhydrous dioxane, and 8 g (6.9 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. At room temperature, 105 g (333 mmol) of tributylvinyltin are added slowly, and after the addition has ended, the mixture is heated at reflux for 21 h. The reaction solution is allowed to cool and filtered through kieselguhr. The filter cake is washed with ethyl acetate and the combined organic filtrates are concentrated to dryness under reduced pressure. The residue that remains is dissolved in dichloromethane and applied to kieselguhr. The product is chromatographed on 1.2 kg of silica gel using a gradient of cyclohexane and ethyl acetate. The product-containing fractions are combined and concentrated to dryness under reduced pressure. This gives 23 g (29% of theory) of the desired product.

Workup

  1. additionafter the addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 21 h
  4. temperatureto cool
  5. filtrationfiltered through kieselguhr
  6. washThe filter cake is washed with ethyl acetate
  7. concentrationthe combined organic filtrates are concentrated to dryness under reduced pressure
  8. dissolutionThe residue that remains is dissolved in dichloromethane
  9. customThe product is chromatographed on 1.2 kg of silica gel using a gradient of cyclohexane and ethyl acetate
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2711c33360944690a0e7968780759bce
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

Loading…