2-(Tributylstannyl)furan → HCID 9890588, compound

HRID 1634289Notes

Reaction equation

HRID 1634289 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]2[C:20]3=[C:21]4[C:26](=[CH:27][CH:28]=[C:19]3[C:12]3[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:11]=3[O:10]2)[NH:25][C:24]([CH3:30])([CH3:29])[CH:23]=[C:22]4[CH3:31])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:37]1[O:38][CH:39]=[CH:40][CH:41]=1)CCC>CN1CCCC1=O.C(OCC)(=O)C.[F-].[K+]>[O:38]1[CH:39]=[CH:40][CH:41]=[C:37]1[C:2]1[CH:3]=[C:4]([CH:9]2[C:20]3=[C:21]4[C:26](=[CH:27][CH:28]=[C:19]3[C:12]3[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:11]=3[O:10]2)[NH:25][C:24]([CH3:30])([CH3:29])[CH:23]=[C:22]4[CH3:31])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 9826255HCID 9826255, compound

Product 1

HCID 9890588HCID 9890588, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Example 11 (0.253 g, 0.531 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was deoxygenated with nitrogen, treated with 2-(tributylstannyl)furan (0.33 mL, 1.06 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.045 g, 0.005 mmol), heated to 85° C. for 13 hours, cooled to room temperature, diluted with ethyl acetate and saturated KF, stirred for 3 hours, and extracted with ethyl acetate. The extract was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel with 5-10% ethyl acetate/hexanes to provide the desired compound.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel with 5-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-de50d8bbfb5a4524a3000aea7e3d5427
Source dataset
uspto-grants-2003_01
Patent number
US06506766B1

Reaction notes

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