Tributylvinyltin → HCID 22050300, compound

HRID 1867060Notes

Reaction equation

HRID 1867060 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:10][C:9]2=[O:25])=[C:4]([CH3:26])[CH:3]=1.[CH2:27]([Sn](CCCC)(CCCC)C=C)[CH2:28]CC>C1COCC1.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>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:11]1[CH:12]=[C:13]([CH3:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:27]=[CH2:28])=[CH:3][C:4]=2[CH3:26])[C:9](=[O:25])[CH:10]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 22050777HCID 22050777, compound

Product 1

HCID 22050300HCID 22050300, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In a 50 ml round bottom flask previously evacuated and filled with nitrogen, 1-(4-bromo-2-methylphenyl)-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (0.420 g, 1.0 mmol) was dissolved in dry THF (10 mL). To this mixture was added Pd (PPh3)4 (0.173 g, 0.15 mmol). The reaction flask was sealed with a rubber septum, evacuated and filled with nitrogen. Under a nitrogen atmosphere, tributyl(vinyl)tin (0.35 ml, 1.2 mmol) was added to the sealed reaction mixture and stirred overnight at 50° C.

Workup

  1. customIn a 50 ml round bottom flask previously evacuated
  2. customThe reaction flask was sealed with a rubber septum
  3. customevacuated
  4. additionfilled with nitrogen

Sources & evidence

ORD record
ord-25db6121b98747b8be76b26866ccd591
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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