Pyridine → 4-benzyloxy-1-{4-[tert-butyl(dimethyl)silyloxy]phenyl}-1H-pyridin-2-one

HRID 15031

Reaction equation

HRID 15031 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:16]([O:23][C:24]1[CH:29]=[CH:28][C:27](OB(O)O)=[CH:26][CH:25]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CC=CC=1.ClCCl>O.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:27]2[CH:28]=[CH:29][C:24]([O:23][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])=[CH:25][CH:26]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 218688774-[Tert-butyl(dimethyl)silyloxy]phenyboric acid

Product 1

HCID 684303014-benzyloxy-1-{4-[tert-butyl(dimethyl)silyloxy]phenyl}-1H-pyridin-2-oneYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-benzyloxy-1H-pyridin-2-one (200 mg, 0.994 mmol), 4-[tert-butyl(dimethyl)silyloxy]phenyboric acid (752 mg, 2.98 mmols), cupric acetate (270 mg, 1.49 mmols), pyridine (0.08 mL, 1.99 mmols) molecular sieve 4A (220 mg) and dichloromethane (4 mL) was stirred for 3 days at room temperature. Chloroform and water were added to the reaction liquid and the insoluble matter was filtered off. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300, methanol:chloroform=1:100) to provide the title compound (234 mg, 58%).

Workup

  1. filtrationthe insoluble matter was filtered off
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe resulting residue was purified on silica gel column chromatography (C-300, methanol:chloroform=1:100)

Sources & evidence

ORD record
ord-55178c8f624d4e63aaba637b697800cf
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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