Imidazole → 4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-3-fluoropyridine

HRID 1046811Notes

Reaction equation

HRID 1046811 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][OH:10])[CH:5]=[CH:4][N:3]=1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].C(Cl)Cl>CN(C=O)C>[Si:20]([O:10][CH2:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 54759140(2-Chloro-3-Fluoropyridin-4-Yl)Methanol

Product 1

HCID 591391774-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-3-fluoropyridineYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-chloro-3-fluoropyridin-4-yl)-methanol (200 mg, 1.24 mmol), imidazole (253 mg, 3.72 mmol) and tert-butyldimethylchlorosilane (373 mg, 2.48 mmol) in DMF was stirred at room temperature for 2 hours. Methylene chloride was then added to the reaction solution, and the solution was washed with saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel column chromatography to yield the title compound (319 mg, 93%).

Workup

  1. washthe solution was washed with saturated saline
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2339fb3a1dff4d7e88109e9c29775343
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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