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

HRID 1948201

反応式

HRID 1948201 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f1a033baa6394e649dbefcb8b87bcc82
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

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