Imidazole → 2-Iodo-5-[[tris(1-methylethyl)silyl]oxy]pyridine

HRID 1685414Notes

Reaction equation

HRID 1685414 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([I:8])=[N:6][CH:7]=1.[CH:9]([Si:12](Cl)([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10].N1C=CN=C1>C(#N)C>[I:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][Si:12]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:9]([CH3:11])[CH3:10])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 110639836-iodopyridin-3-ol

Product 1

HCID 866250242-Iodo-5-[[tris(1-methylethyl)silyl]oxy]pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 g (22.6 mM) of 5-hydroxy-2-iodopyridine and 6.42 ml (30.09 mM) of triisopropylsilyl chloride in 35 ml of acetonitrile are stirred at room temperature for 10 minutes. After the addition of 4.62 g (67.87 mM) of imidazole, stirring is maintained for 4 h 20 min at room temperature. The acetonitrile is evaporated off and the reaction mixture is taken up with three 150 ml portions of pentane. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is passed through a silica plug using petroleum ether as the eluent to give the desired product in the form of a light yellow oil with a yield of 98%.

Workup

  1. customThe acetonitrile is evaporated off
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-400f5292a98840968fefd02f64738cd8
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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