Dimethylformamide → 3-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile

HRID 1511075노트

반응식

HRID 1511075 반응식
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[S:7].Br[C:9]1[CH:10]=[C:11]([O:17][C:18]2[C:19]([CH3:25])=[N:20][CH:21]=[CH:22][C:23]=2[CH3:24])[C:12]([C:15]#[N:16])=[N:13][CH:14]=1.CN(C=O)C.[H-].[Na+]>O>[CH3:25][C:19]1[C:18]([O:17][C:11]2[C:12]([C:15]#[N:16])=[N:13][CH:14]=[C:9]([S:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:10]=2)=[C:23]([CH3:24])[CH:22]=[CH:21][N:20]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27236982-MercaptopyridineHCID 674859525-Bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile

생성물 1

HCID 674858013-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile수율 92.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

Pyridin-2(1H)-thione (0.768 g, 6.90 mmol) and 5-bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile (2.00 g, 6.58 mmol) were added to DMF (12 mL) and cooled to 0° C. 95% Sodium hydride (0.174 g, 6.90 mmol) was slowly added and the reaction was warmed to ambient temperature and stirred overnight. The reaction mixture was poured into water (100 mL) and stirred for 30 minutes. A cloudy milky solution that was not filterable resulted. The reaction was extracted twice with ethyl acetate. The combined organic layers were washed twice with water and brine, dried, and concentrated. The residue was purified over silica gel (2:3 to 0:1 hexane:ethyl acetate) to afford 3-(2,4-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (2.03 g, 6.07 mmol, 92.3% yield) as a white powder.

후처리

  1. temperaturethe reaction was warmed to ambient temperature
  2. stirringstirred for 30 minutes
  3. extractionThe reaction was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed twice with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified over silica gel (2:3 to 0:1 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-76342b4b6d9742f09bf7d27b8a4dd8fb
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212045B2

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