2-(Tri-n-butylstannyl)thiophene → HCID 86754225, compound

HRID 581903Notes

Reaction equation

HRID 581903 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)CCC>CN(C=O)C.O>[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[CH:13]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 54320977HCID 54320977, compound

Product 1

HCID 86754225HCID 86754225, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 29a from Example 8 (0.7 g, 2.1 mmol), 2-(tributylstannyl)thiophene (1.59 g, 4.3 mmol) and tris(triphenylphosphine)palladium dichloride (50 mg) in DMF (5 ml) is heated to 80° C. over night. The cooled reaction mixture is diluted with 4 volumes of water and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 0.56 g (80%). Mp 184-185° C.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts are dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column-chromatography on silica gel using
  6. additiona mixture of ethyl acetate and petroleum ether (1:1) as the eluent

Sources & evidence

ORD record
ord-d1bd144fc16843c89ef86a1c0821d017
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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