Potassium Carbonate → 1-(cyclohexylmethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

HRID 1948201Notes

Reaction equation

HRID 1948201 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(#N)C>[CH:24]1([CH2:23][N:13]2[CH:14]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=[CH:11][C:12]2=[O:15])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 200814975-(4-Methoxyphenyl)pyridin-2(1H)-one

Product 1

HCID 589669191-(cyclohexylmethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-oneYield 31.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 5 Step 2: To a solution of 5-(4-methoxyphenyl)pyridin-2(1H)-one (1 eq, 0.35 mmol, 70 mg, Example 7 Step 1) in acetonitrile (2 mL) were added K2CO3 (10 eq, 3.50 mmol, 0.48 g) and (bromomethyl)cyclohexane (10 eq, 3.50 mmol, 0.49 mL). The reaction was microwaved for 10 minutes at 180° C. The reaction was allowed to cool. The reaction was then filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 15 g SiO2) using CH2Cl2/AcOEt (80/20, Rf=0.3). The product was further purified by reverse phase C18 column using water/acetonitrile 60/40 to afford 1-(cyclohexylmethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.11 mmol, 32 mg, 31%) as a colorless oil.

Workup

  1. customThe reaction was microwaved for 10 minutes at 180° C
  2. temperatureto cool
  3. filtrationThe reaction was then filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 15 g SiO2)
  6. customThe product was further purified by reverse phase C18 column

Sources & evidence

ORD record
ord-f1a033baa6394e649dbefcb8b87bcc82
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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