Tributylstannane → HCID 9842511, compound

HRID 1421498Notes

Reaction equation

HRID 1421498 reaction equation
[C:1]([C:3]1[C:7]([CH:8]2[CH2:11][C:10](=[O:12])[C:9]2(Cl)Cl)=[CH:6][N:5]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[N:4]=1)#[N:2].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:3]1[C:7]([CH:8]2[CH2:9][C:10](=[O:12])[CH2:11]2)=[CH:6][N:5]([C:15]2[C:16]([Cl:26])=[CH:17][C:18]([C:22]([F:23])([F:24])[F:25])=[CH:19][C:20]=2[Cl:21])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 9911260HCID 9911260, compound

Product 1

HCID 9842511HCID 9842511, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
2 °C

Procedure

3-Cyano-4-(2,2-dichloro-3-oxocyclobutyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (3.00 g, 6.77 mmol, Example 1) was dissolved in dry toluene (60 ml) in a dry, nitrogen-flushed flask and cooled to 2° C. 2,2'-Azobisisobutyronitrile (134 mg, 0.81 mmol) was added in one portion followed by dropwise addition of tributyltin hydride (4.73 ml, 17.60 mmol) in dry toluene (10 ml). The mixture was allowed to slowly warm to room temperature and was stirred for 18 hr. The toluene was removed in vacuo and the residue dissolved in acetonitrile (50 ml). This solution was washed with hexane (4×50 ml) to remove organotin residues. The combined hexane fractions were extracted with acetonitrile (50 ml). The acetonitrile phases were combined and the solvent removed in vacuo to give a yellow oil. This was purified by silica chromatography (eluting with 10% diethyl ether/hexane) to yield 2.07 g of the title compound as a white solid.

Workup

  1. customflushed flask
  2. temperatureto slowly warm to room temperature
  3. customThe toluene was removed in vacuo
  4. dissolutionthe residue dissolved in acetonitrile (50 ml)
  5. washThis solution was washed with hexane (4×50 ml)
  6. customto remove organotin residues
  7. extractionThe combined hexane fractions were extracted with acetonitrile (50 ml)
  8. customthe solvent removed in vacuo
  9. customto give a yellow oil
  10. customThis was purified by silica chromatography (eluting with 10% diethyl ether/hexane)

Sources & evidence

ORD record
ord-ed023016f13b4680828b82f9a786bcc0
Source dataset
uspto-grants-2000_06
Patent number
US06077859

Reaction notes

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