Azido(trimethyl)stannane → HCID 178525022, compound

HRID 277980Notes

Reaction equation

HRID 277980 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1)#[N:2].[N:25]([Sn](C)(C)C)=[N+:26]=[N-:27]>C1(C)C=CC=CC=1>[NH:25]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]2[C:10]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:2][N:27]=[N:26]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 7520286HCID 7520286, compound

Product 1

HCID 178525022HCID 178525022, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of benzyl 2′-cyano-2-bipheylcarboxylate (560 mg) in toluene (10 ml), azidotrimethyltin (810 mg) was added. The mixture was refluxed for 12 hours. The reaction mixture was concentrated. 5% aqueous solution of potassium fluoride (4 ml) was added to the residue. The solution was filtered. The filtrate was diluted with ethyl acetate, and the solution was washed with a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→chloroform:methanol=10:1) to give the title compound (545 mg) having the following physical data.

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. concentrationThe reaction mixture was concentrated
  3. addition5% aqueous solution of potassium fluoride (4 ml) was added to the residue
  4. filtrationThe solution was filtered
  5. additionThe filtrate was diluted with ethyl acetate
  6. washthe solution was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-559c0fe0218d4d70acffed483075542d
Source dataset
uspto-grants-2002_03
Patent number
US06358960B1

Reaction notes

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