Dibutyltin oxide → HCID 178497606, compound

HRID 2378059Notes

Reaction equation

HRID 2378059 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3([CH2:25][C:26]#[N:27])[CH2:24][CH2:23]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.C([Sn](=O)CCCC)CCC.[N:38]([Si](C)(C)C)=[N+:39]=[N-:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([C:22]3([CH2:25][C:26]4[NH:40][N:39]=[N:38][N:27]=4)[CH2:23][CH2:24]3)[O:13][N:12]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 68958470HCID 68958470, compound

Product 1

HCID 178497606HCID 178497606, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture consisting of {1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropyl}-acetonitrile (the synthetic intermediate prepared in Example 42, Step A, 0.7 g) in toluene (10 mL) are added di-n-butyltin oxide (0.48 g) and azidotrimethylsilane (0.51 mL.) The stirring mixture is brought to reflux and continued stirring overnight. The mixture is subsequently cooled to room temperature, diluted with ethyl acetate (40 mL), and sequentially washed with water (20 mL) and brine solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (1:1 v/v) and further elution with ethyl acetate afforded the synthetic intermediate 5-{1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-1H-tetrazole (0.6 g.)

Workup

  1. temperatureto reflux
  2. washsequentially washed with water (20 mL) and brine solution (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate is purified by flash silica gel column chromatography
  7. washElution
  8. washwith hexanes-ethyl acetate (1:1 v/v) and further elution with ethyl acetate

Sources & evidence

ORD record
ord-00e7299e4db246d5be92ab587691558b
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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