Tributylstannane → HCID 71272389, compound

HRID 475081Notes

Reaction equation

HRID 475081 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13]3(OC(SC)=S)[CH2:16][O:15][CH2:14]3)[N:10]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:14][O:15][CH2:16]3)[N:10]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86694685HCID 86694685, compound

Product 1

HCID 71272389HCID 71272389, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Into a 2 L round-bottom flask under nitrogen was placed a solution of ([3-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-5-yl]oxetan-3-yl]oxy)(methylsulfanyl)methanethione (97.0 g, 213.8 mmol, 1.0 equiv.) in toluene (1.2 L), tributyltin hydride (74.7 g, 256.7 mmol, 1.2 equiv.), and AIBN (7.0 g, 42.6 mmol, 0.2 equiv.). The resulting solution was stirred at 120° C. for 3 h, cooled to 30° C. and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/PE (1:100-1:5) to afford 3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(oxetan-3-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole (30.0 g, 38% yield) as a yellow oil.

Workup

  1. customInto a 2 L round-bottom flask under nitrogen was placed
  2. temperaturecooled to 30° C.
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by SiO2 chromatography
  5. washeluting with EtOAc/PE (1:100-1:5)

Sources & evidence

ORD record
ord-6f21a29d23504e6286cfa070a36a1c2e
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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