Tributylstannane → HCID 86687892, compound

HRID 868932Notes

Reaction equation

HRID 868932 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]=[C:7]1[CH:17]=[O:18].N(/C(C)(CC)C#N)=N\C(C)(CC)C#N.C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C(#N)C>[C:11]1([C:9]2[N:8]=[C:7]([CH:17]=[O:18])[N:6]3[CH2:5][CH2:4][CH2:3][CH2:2][C:10]=23)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86687891HCID 86687891, compoundHCID 178446861HCID 178446861, compound

Product 1

HCID 86687892HCID 86687892, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(4-bromobutyl)-4-phenyl-1H-imidazole-2-carbaldehyde (918 mg, 3 mmol) in dry acetonitrile (300 mL) was heated at reflux. (E)-2,2′-(Diazene-1,2-diyl)bis(2-methylbutanenitrile) (AIBN) (288 mg, 1.5 mmol) was added followed by addition of tributylstannane (1.93 g, 6.6 mmol) over the course of 2 hours. An additional aliquot of AIBN (288 mg, 1.5 mmol) was added 1 hour after the start of the reaction. The mixture was stirred under reflux for 2 hours. Acetonitrile was removed under reduced pressure. The obtained residue was purified by column chromatography to give 1-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine-3-carbaldehyde as a white solid (250 mg). MS (ESI): m/z 227 (M+H)+.

Workup

  1. temperatureat reflux
  2. customafter the start of the reaction
  3. temperatureunder reflux for 2 hours
  4. customAcetonitrile was removed under reduced pressure
  5. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-ee9ab01f49744e2bb94a5e14cec6941d
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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