Potassium Carbonate → 1-(3-fluoro-4-(morpholinomethyl)phenyl)-3,5-dimethylpyridin-2(1H)-one

HRID 56074ノート

反応式

HRID 56074 の反応式
[CH3:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:23]=[C:22](I)[CH:21]=[CH:20][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CN(C=O)C>[F:10][C:11]1[CH:23]=[C:22]([N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]2=[O:9])[CH:21]=[CH:20][C:12]=1[CH2:13][N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 123485383,5-Dimethyl-1,2-dihydropyridin-2-oneHCID 900233414-(2-Fluoro-4-iodobenzyl)morpholine

生成物 1

HCID 729506741-(3-fluoro-4-(morpholinomethyl)phenyl)-3,5-dimethylpyridin-2(1H)-one収率 50%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3,5-dimethylpyridin-2(1H)-one (0.22 g, 1.80 mmol), 4-(2-fluoro-4-iodobenzyl)morpholine (0.58 g, 1.80 mmol), K2CO3 (2.48 g, 18 mmol), CuI (0.02 g, 0.1 mmol) and DMF (3 mL) was refluxed under N2. The reaction process was monitored by TLC. The reaction mixture was cooled to rt and filtered. To the filtrate was added H2O (10 mL) and CH2Cl2 (20 mL). The CH2Cl2 layer was separated, and the aqueous layer was extracted with CH2Cl2 (20 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (0.28 g, 50%). The compound was characterized by the following spectroscopic data:

後処理

  1. temperaturewas refluxed under N2
  2. filtrationfiltered
  3. additionTo the filtrate was added H2O (10 mL) and CH2Cl2 (20 mL)
  4. customThe CH2Cl2 layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (20 mL×2)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

出典と根拠

ORDレコード
ord-148628301ca345b98164581c419f0219
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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