Acetonitrile → 5-(4-methoxyphenyl)-1-(2-phenoxyethyl)pyridin-2(1H)-one

HRID 1948199

反応式

HRID 1948199 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][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(#N)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[N:13]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:14]=2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium Carbonate2 回HCID 68526Benzene, (2-bromoethoxy)-2 回HCID 200814975-(4-Methoxyphenyl)pyridin-2(1H)-one

生成物 1

HCID 589669325-(4-methoxyphenyl)-1-(2-phenoxyethyl)pyridin-2(1H)-one収率 44%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

According to Scheme 5 Step 2: To a solution of 5-(4-methoxyphenyl)-(1H)-pyridin-2-one (1 eq, 0.30 mmol, 60 mg) in THF (3 mL) was added K2CO3 (10 eq, 3.00 mmol, 0.41 g). The reaction was stirred at room temperature for 30 minutes then 1-(2-bromoethoxy)benzene (3 eq, 0.90 mmol, 0.18 g) was added. The reaction was stirred at 60° C. for 12 hours. After concentration of the solvent, acetonitrile (3 mL) was added followed by K2CO3 (10 eq, 3.00 mmol, 0.41 g) and 1-(2-bromoethoxy)benzene (10 eq, 3.00 mmol, 0.60 g) then the reaction was microwaved for 5 minutes at 180° C. The reaction was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2) using CH2Cl2/AcOEt (80/20) as the eluent to afford 5-(4-methoxyphenyl)-1-(2-phenoxyethyl)pyridin-2(1H)-one (0.13 mmol, 42 mg, 44%) as a yellow oil.

後処理

  1. stirringThe reaction was stirred at 60° C. for 12 hours
  2. customthe reaction was microwaved for 5 minutes at 180° C
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2)

出典と根拠

ORDレコード
ord-2aa05178150b4cd185800356bf605313
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

関連ノート

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