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

HRID 1948201

반응식

HRID 1948201 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f1a033baa6394e649dbefcb8b87bcc82
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

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