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

HRID 401505

반응식

HRID 401505 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 222Ammonia용매

반응 조건

온도
135 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-888f00936297475e8020806961d426d4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741936B2

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