Tributylvinyltin → HCID 57470605, compound

HRID 602056Notes

Reaction equation

HRID 602056 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[C:6](OC(=O)C(F)(F)F)[C:7]=1[F:8].[Cl-].[Li+].[CH:26]([Sn](CCCC)(CCCC)CCCC)=[CH2:27].[F-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:26]([C:6]1[CH:5]=[C:4]([C:16]([CH3:22])([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3]=[C:2]([F:1])[C:7]=1[F:8])=[CH2:27]

Participants

7

Reactant 4

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 68790034HCID 68790034, compound

Product 1

HCID 57470605HCID 57470605, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-{3,4-difluoro-5-[(trifluoroacetyl)oxy]phenyl}-2-methylpropanoate (113 mg, 0.332 mmol) in DMF (6 mL, deoxygenated with N2) under N2 was added (t-Bu3P)2Pd (25 mg, 0.05 mmol), lithium chloride (42 mg, 0.996 mmol), and vinyl(tributyl)tin (0.11 mL, 0.365 mmol). The reaction was stirred at room temperature for 22 hours. To the reaction mixture was added ethyl acetate and 20% KF (aq.) and the reaction stirred for an additional 2 h. The suspension was filtered through and rinsed with ethyl acetate. The organic layer was washed with 20% KF (aq.). The combined aqueous layers were washed with ethyl acetate. The combined organic layers were then washed with H2O and brine, dried, and purified by Biotage purification system using (0-80% DCM:hexane) yielded the desired product (50 mg, 60%).

Workup

  1. stirringthe reaction stirred for an additional 2 h
  2. filtrationThe suspension was filtered through and
  3. washrinsed with ethyl acetate
  4. washThe organic layer was washed with 20% KF (aq.)
  5. washThe combined aqueous layers were washed with ethyl acetate
  6. washThe combined organic layers were then washed with H2O and brine
  7. customdried
  8. custompurified by Biotage purification system

Sources & evidence

ORD record
ord-18a7652a259d4ad58afa2c045eea2431
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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