Imidazole → HCID 59574609, compound

HRID 2092047Notes

Reaction equation

HRID 2092047 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.C(OCC)(=O)C>ClCCl>[Si:10]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 11332468(2-Fluoropyridin-4-yl)methanol

Product 1

HCID 59574609HCID 59574609, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-4-pyridinemethanol (508.5 mg, 4.00 mmol), t-butyldimethylsilylchloride (1.21 g, 8.00 mmol) and imidazole (1.09 g, 16.00 mmol) were stirred in dichloromethane (10 mL) at room temperature for an hour. After completion of the reaction, the reaction solution was mixed with ethyl acetate, and the resulting organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to give the desired product (785.2 mg, 81% yield).

Workup

  1. customAfter completion of the reaction
  2. washthe resulting organic layer was washed with saturated aqueous ammonium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-13fc3309cb36418485449ae35863fcdd
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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