Stannane, tributyl(1-ethoxyethenyl)- → HCID 16065044, compound

HRID 1360700Notes

Reaction equation

HRID 1360700 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:10](=[O:27])[CH:11]=[CH:12][N:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[C:4]([F:28])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:34]([O:36]CC)=[CH2:35])CCC>C1(C)C=CC=CC=1.O.CCOC(C)=O.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>[C:34]([C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:10](=[O:27])[CH:11]=[CH:12][N:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[C:4]([F:28])[CH:3]=1)(=[O:36])[CH3:35]

Participants

7

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 16065043HCID 16065043, compound

Product 1

HCID 16065044HCID 16065044, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-bromo-2,6-difluorophenyl)-6-(2,4-difluorophenyl)-2H-quinolizin-2-one (30 mg, 0.067 mmol) in toluene (1.4 mL) was added tributyl(1-ethoxyvinyl)stannane and tetrakis(triphenylphosphine)palladium (7.74 mg, 0.007 mmol) and heated to 90° C. for 1½ h. The reaction was cooled, filtered through celite, and diluted with THF. The mixture was added 2N HCl and stirred for 20 min to complete the reaction. The crude mixture was diluted with H2O and EtOAc. The organic layer was washed with H2O, brine, dried over MgSO4, and condensed. The crude residue was purified via silica gel chromatography (hexanes/ethyl acetate) to give the title compound (7.9 mg).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through celite
  3. additiondiluted with THF
  4. additionThe mixture was added 2N HCl
  5. customthe reaction
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialdried over MgSO4, and condensed
  8. customThe crude residue was purified via silica gel chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-df881b32556a405586587685ca113cfe
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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