Cesium carbonate → 1-(3-fluoro-4-(morpholinomethyl)phenyl)-5-methylpyridin-2(1H)-one

HRID 56073

反応式

HRID 56073 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].O=C1CCCCC1C(OCC)=O.[CH3:19][C:20]1[CH:21]=[CH:22][C:23](=[O:26])[NH:24][CH:25]=1.[F:27][C:28]1[CH:40]=[C:39](I)[CH:38]=[CH:37][C:29]=1[CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CS(C)=O.[Cu]I>[F:27][C:28]1[CH:40]=[C:39]([N:24]2[CH:25]=[C:20]([CH3:19])[CH:21]=[CH:22][C:23]2=[O:26])[CH:38]=[CH:37][C:29]=1[CH2:30][N:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 704822-Hydroxy-5-methylpyridineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 900233414-(2-Fluoro-4-iodobenzyl)morpholine

生成物 1

HCID 729506711-(3-fluoro-4-(morpholinomethyl)phenyl)-5-methylpyridin-2(1H)-one収率 23.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

A mixture of CuI (0.19 g, 1 mmol), Cs2CO3 (6.85 g, 20 mmol) and ethyl 2-oxocyclohexanecarboxylate (0.34 g, 2 mmol) in DMSO (10 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 5-methylpyridone (1.09 g, 10 mmol) and 4-(2-fluoro-4-iodobenzyl) morpholine (3.21 g, 10 mmol) in DMSO (12 mL) via syringe. The reaction mixture was heated at 100° C. overnight, cooled to rt and filtered. The filtrate diluted with H2O (50 mL) was extracted with CH2Cl2 (50 mL×3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as a white solid (0.70 g, 23%). The compound was characterized by the following spectroscopic data:

後処理

  1. temperatureThe reaction mixture was heated at 100° C. overnight
  2. temperaturecooled to rt
  3. filtrationfiltered
  4. additionThe filtrate diluted with H2O (50 mL)
  5. extractionwas extracted with CH2Cl2 (50 mL×3)
  6. concentrationThe combined organic phases were concentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

出典と根拠

ORDレコード
ord-f91fcb89faa24fb3b96e7ae030830ad4
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

関連ノート

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