Tri(butyl)vinylstannane → HCID 54049649, compound

HRID 2170951Notes

Reaction equation

HRID 2170951 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:8]=1[CH:15]=[O:16])(=O)=O.[CH2:19](C([SnH3])=C(CCCC)CCCC)[CH2:20]CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:15]([C:8]1[CH:9]=[CH:10][C:11]([C:13]#[N:14])=[CH:12][C:7]=1[CH:19]=[CH2:20])=[O:16]

Participants

4

Reactant 2

HCID 21115800Tri(butyl)vinylstannaneHCID 593496385-Cyano-2-formylphenyl trifluoromethanesulfonate

Product 1

HCID 54049649HCID 54049649, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

125 mg (0.18 mmol) of bis(triphenylphosphine)palladium(II) chloride are added to a solution of 1 g (3.58 mmol) of 5-cyano-2-formylphenyl trifluoromethanesulfonate and 1.15 ml (3.94 mmol) of tri-n-butylvinylstannane in 6 ml of anhydrous and degassed DMF under an argon atmosphere. The reaction mixture is then stirred at 80° C. for 90 min. Subsequently, 100 ml of 10% strength potassium fluoride solution are added, and the mixture is stirred at RT for 1 h. The suspension is extracted three times with 20 ml of ethyl acetate each time, and the combined organic phases are washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic solution is dried over magnesium sulfate and concentrated. The residue (0.6 g) is employed without further purification in the next stage.

Workup

  1. customdegassed DMF under an argon atmosphere
  2. additionSubsequently, 100 ml of 10% strength potassium fluoride solution are added
  3. stirringthe mixture is stirred at RT for 1 h
  4. extractionThe suspension is extracted three times with 20 ml of ethyl acetate each time
  5. washthe combined organic phases are washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  6. dry with materialThe organic solution is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue (0.6 g) is employed without further purification in the next stage

Sources & evidence

ORD record
ord-fd1067736ccb4c048eaf1109a2586fd2
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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