Dibutyltin oxide → HCID 10016619, compound

HRID 2055731Notes

Reaction equation

HRID 2055731 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:19]([Si](C)(C)C)=[N+:20]=[N-:21].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([C:8]([C:9]2[N:19]=[N:20][NH:21][N:10]=2)([CH3:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 58616026HCID 58616026, compound

Product 1

HCID 10016619HCID 10016619, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(2-fluoro-biphenyl-4-yl)-2-methyl-propionitrile (100 mg, 0.418 mmol), azidotrimethylsilane (222 μL, 1.672 mmol) and dibutyltin oxide (20 mg) in dry toluene (2.5 mL) was heated under microwave irradiation in a sealed vessel at 150° C. for 1000 seconds. The solution was then diluted with EtOAc, washed with water, the organics separated, dried (MgSO4), filtered and evaporated to dryness. The residue was purified by column chromatography (EtOAc) to afford the title compound, 5-[1-(2-Fluoro-biphenyl-4-yl)-1-methyl-ethyl]-2H-tetrazole as a colorless powder. 1H NMR (500 MHz, CD3OD) δ 7.50 (2H, m), 7.40-7.46 (3H, m), 7.35 (1H, m), 7.05-7.12 (2H, m), 1.87 (6H, s). LCMS(EI) 283.1 (M+H)+, 324.2 (M+Na+H3O)+.

Workup

  1. washwashed with water
  2. dry with materialthe organics separated, dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-78b7b9bc3a9a4932b6fbad4558c279cb
Source dataset
uspto-grants-2008_02
Patent number
US07332516B2

Reaction notes

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