Dimethylformamide → 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

HRID 534102노트

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HRID 534102 반응식
Br[C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].CN(C=O)C.[H-].[Na+]>O>[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 674868715-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrileHCID 178418616HCID 178418616, 화합물

생성물 1

HCID 674864015-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile수율 96.7%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

A flask was charged with 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (27.77 g, 90.41 mmol), pyridine-2-thiol (10.55 g, 94.93 mmol), and DMF (300 mL). The reaction was cooled to 0° C. and 95% sodium hydride (2.741 g, 108.5 mmol) was added portionwise. The reaction was stirred at ambient temperature overnight, then carefully diluted with water (2 L) and extracted with ethyl acetate. The organic layer was washed with brine (4×500 mL), dried over sodium sulfate and concentrated to afford 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (29.50 g, 87.43 mmol, 96.70% yield) as yellow solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine (4×500 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f3be4bd4c6104e7fa6e03fbe14fbfe17
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853409B2

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