Dimethylformamide → 2(1H)-Pyridinone,1-(4-methoxyphenyl)-5-(trifluoromethyl)-

HRID 401505

反応式

HRID 401505 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6](=[O:9])[NH:7][CH:8]=1.I[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>N.[Cu]I>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([N:7]2[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=[CH:5][C:6]2=[O:9])=[CH:14][CH:15]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridine

生成物 1

HCID 119889442(1H)-Pyridinone,1-(4-methoxyphenyl)-5-(trifluoromethyl)-収率 39.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 222Ammonia溶媒

反応条件

温度
135 °C

実験手順

A mixture of 5-(trifloromethyl)-2(1H)-pyridone (815.5 mg, 5 mmol), 4-iodoanisole (2.34 g, 10 mmol), CuI (952 mg, 5 mmol), K2CO3 (691 mg, 5 mmol) and DMF (5 ml) was heated at 135° C. overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. Column chromatography purification (30% ethyl acetate-hexane) afforded 526 mg (39.2%) of 1-(4-methoxyphenyl)-5-(trifloromethyl)-2-pyridone. This compound (268.2 mg, 1 mmol) was treated with 1M BBr3 solution in dichloromethane (DCM, 2 ml) in DCM (5 ml) for 2 hours at 0° C. Reaction mixture was diluted with DCM and washed 3 times with water. Organic phase was dried over sodium sulfate and evaporated. The residue was separated by column chromatography (20% ethyl acetate-DCM) to afford the title compound as an off-white solid, 226 mg (89%). The 1H NMR spectra was consistent with the structure of Compound 10.

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customColumn chromatography purification (30% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-888f00936297475e8020806961d426d4
出典データセット
uspto-grants-2014_06
特許番号
US08741936B2

関連ノート

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