Cesium carbonate → 6-(3-Fluoroazetidin-1-yl)-2-methyl-3-nitropyridine

HRID 510481노트

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HRID 510481 반응식
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:18][CH:19]1[CH2:22][NH:21][CH2:20]1>CN(C=O)C.CCOC(C)=O>[F:18][CH:19]1[CH2:22][N:21]([C:2]2[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=2)[CH2:20]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 36035423-Fluoroazetidine

생성물 1

HCID 895591516-(3-Fluoroazetidin-1-yl)-2-methyl-3-nitropyridine수율 98%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 6-chloro-2-methyl-3-nitropyridine (0.5 g, 2.9 mmol) in DMF (5 mL) was added Cs2CO3 (1.9 g, 5.8 mmol) followed 3-fluoroazetidine (0.64 g, 5.8 mmol) and the reaction mixture was heated for 2 h at 80° C. The reaction mixture was then diluted with EtOAc and the organic layer was washed with saturated aqueous sodium bicarbonate solution. The organic layer was then dried over sodium sulphate and concentrated. The crude material obtained was purified by column chromatography (silica: 100-200 mesh, MeOH:DCM 2-3%) to afford the title compound (0.6 g, 92%). LCMS (ES+) 211.95 (M+H)+, RT 2.33 minutes (method 1).

후처리

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was then dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe crude material obtained
  5. customwas purified by column chromatography (silica: 100-200 mesh, MeOH:DCM 2-3%)

출처 및 근거

ORD 기록
ord-091cf670ef17446db971cfd83348d3b7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096614B2

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