Water → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

HRID 452209Notes

Reaction equation

HRID 452209 reaction equation
CC(C)([O-])C.[K+].[Si:7]([O:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:33][C:34]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[CH:36][C:35]=1F.O>CN(C=O)C>[Si:7]([O:24][CH2:25][C:26]1[C:27](=[O:32])[N:28]([C:35]2[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:34]=2[Cl:33])[CH:29]=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:21])[CH3:22])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 23665647Potassium tert-butoxideHCID 594101563-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

Product 1

HCID 594101863-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C., 0.500 g (4.46 mmol) of potassium tert-butoxide is added to 1.08 g (2.97 mmol) of the compound from Example 3A in 21 ml of DMF, and the mixture is stirred at room temperature for 30 min. 0.571 g (3.27 mmol) of 2-chloro-1-fluoro-4-nitrobenzene is added, and the mixture is stirred at RT. After 4.5 h, 200 ml of water are added, and the mixture is then extracted three times with ethyl acetate. The combined organic phases are washed with water and then dried over sodium sulphate. After filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1). This gives 872 mg (56% of theory) of the desired compound.

Workup

  1. stirringthe mixture is stirred at RT
  2. waitAfter 4.5 h
  3. extractionthe mixture is then extracted three times with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration
  7. customthe solvents are removed under reduced pressure
  8. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-0b01ac8c612546f89c7576afb6d56dc1
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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