Dibutyltin oxide → HCID 178520625, compound

HRID 1647226Notes

Reaction equation

HRID 1647226 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH2:9][CH:10]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[C:24]#[N:25])[CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])=[CH:4][CH:3]=1.C[Si]([N:34]=[N+:35]=[N-:36])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:29])[CH2:9][CH:10]([C:21]2[CH:28]=[CH:27][CH:26]=[C:23]([C:24]3[NH:36][N:35]=[N:34][N:25]=3)[CH:22]=2)[CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 199264963-[3-(4-Fluorophenyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]-3-oxopropyl]-benzonitrile

Product 1

HCID 178520625HCID 178520625, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-[3-(4-fluorophenyl)-1-[2-(4-fluorophenyl)-2-oxoethyl]-3-oxopropyl]-benzonitrile (1 g, 2.1 mmol), trimethylsilylazide (0.48 g, 4.2 mmol), and dibutyltin oxide (0.05 g) is heated under N2 in toluene (25 mL) at 100° C. for 18 hours. The toluene is removed under vacuum and the residue is dissolved in a small amount of methanol. The methanol is removed under vacuum and the residue chromatographed over SiO2 eluting with dichloromethane:2-propanol (4:1). Pure fractions are combined, concentrated, and triturated with diethyl ether to provide 0.8 g of the title compound; mp 162°-164C.

Workup

  1. customThe toluene is removed under vacuum
  2. dissolutionthe residue is dissolved in a small amount of methanol
  3. customThe methanol is removed under vacuum
  4. customthe residue chromatographed over SiO2 eluting with dichloromethane:2-propanol (4:1)
  5. concentrationconcentrated
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-cc3b5fc3368d4ce384cce6da3dbc0f62
Source dataset
uspto-grants-1995_07
Patent number
US05430047

Reaction notes

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