2-(Tributylstannyl)furan → HCID 68689144, compound

HRID 1159017Notes

Reaction equation

HRID 1159017 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16](Br)=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:32]1[O:33][CH:34]=[CH:35][CH:36]=1)CCC>C1(C)C=CC=CC=1.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:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([C:32]1[O:33][CH:34]=[CH:35][CH:36]=1)=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 16115648HCID 16115648, compound

Product 1

HCID 68689144HCID 68689144, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a degassed solution of tetrakis(triphenylphosphine)palladium(0) (3 mg, 0.002 mmol) in toluene (2 mL) was added N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-bromo-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (50 mg, 0.12 mmol). The resulting solution was degassed by exposure to vacuum and then an argon atmosphere (×3). To this solution was added 2-(tributylstannyl)furan (0.038 mL, 0.12 mmol). The resulting solution was degassed a final time and was then warmed to reflux conditions. The light yellow solution was maintained at reflux conditions for 14 h and became gray in color. The reaction was cooled, diluted with ethyl acetate, aqueous hydrogen chloride (1N), and saturated aqueous sodium chloride. The layers were separated and the aqueous layer washed with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by radial chromatography (10-30% ethyl acetate in hexanes) to give the desired product as a clear residue (44 mg, 90%).

Workup

  1. customThe resulting solution was degassed by exposure to vacuum
  2. customThe resulting solution was degassed a final time
  3. temperaturewas then warmed
  4. temperatureto reflux conditions
  5. temperatureThe light yellow solution was maintained
  6. temperatureat reflux conditions for 14 h
  7. temperatureThe reaction was cooled
  8. additiondiluted with ethyl acetate, aqueous hydrogen chloride (1N), and saturated aqueous sodium chloride
  9. customThe layers were separated
  10. washthe aqueous layer washed with ethyl acetate
  11. dry with materialThe combined organic layers were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe resulting residue was purified by radial chromatography (10-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-792ab4d522694992895984d4a1877d74
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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