Tributylvinyltin → HCID 18379026, compound

HRID 2298982Notes

Reaction equation

HRID 2298982 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:29]([Sn](CCCC)(CCCC)C=C)[CH2:30]CC>C1(C)C=CC=CC=1.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:29]=[CH2:30])[CH:21]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 154896306-(4-Chloro-benzoyl)4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-one

Product 1

HCID 18379026HCID 18379026, compoundYield 85.8%

Reagents, catalysts & solvents 3

HCID 821241,4-Bis(diphenylphosphino)butaneCatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 1,4-bis(diphenylphosphine)butane (120 mg, 0.28 mMol) in toluene (15 mL) was added dichlorobis(benzonitrile)palladium(II) (108 mg, 0.28 mMol) under an atmosphere of dry N2. The reaction mixture was stirred at ambient temperature for 45 minutes after which time the solution was diluted with toluene (85 mL). To this solution was added 6-(4-chloro-benzoyl)-4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-one (14.0 g, 28.0 mMol) and tributyl(vinyl)tin (9.1 mL, 32.9 mMol). The reaction was heated to reflux and stirred at this temperature for 1 hour. The reaction mixture was concentrated under vacuum and chromatographed on flash silica gel eluting DCM until the tin impurities had eluted. The product was eluted off with DCM/MeOH (99:1) to give 9.61 g of the titled compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. stirringstirred at this temperature for 1 hour
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. customchromatographed on flash silica gel
  6. washeluting DCM until the tin impurities
  7. washhad eluted
  8. washThe product was eluted off with DCM/MeOH (99:1)

Sources & evidence

ORD record
ord-4ecc4dd1316c419485b48e657f760aaf
Source dataset
uspto-grants-2002_12
Patent number
US06495564B1

Reaction notes

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