Dibutyltin oxide → HCID 178466679, compound

HRID 510843Notes

Reaction equation

HRID 510843 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH3:19])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[N:21]([Si](C)(C)C)=[N+:22]=[N-:23].C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1>[Cl:20][C:6]1[C:7]([CH3:19])=[C:8]([C:17]2[NH:23][N:22]=[N:21][N:18]=2)[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

Product 1

HCID 178466679HCID 178466679, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-carbonitrile (100 mg, 0.3 mmol), azidotrimethylsilane (0.092 mL, 0.69 mmol), and dibutyloxostannane (13 mg, 0.052 mmol) in toluene (2.9 mL) was heated at reflux overnight. The mixture was evaporated to dryness and purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product (85 mg, 70%). LCMS calculated for C16H13ClFN4O (M+H)+: m/z=331.1. found: 331.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica gel
  5. washeluting with 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ec571eb1cb6548bab1984680df6919c1
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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