1H-1,2,4-Triazole → 3-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile

HRID 397516노트

반응식

HRID 397516 반응식
[C:1]([C:3]1[C:8](F)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1>CN(C=O)C.O>[N:16]1([C:8]2[C:3]([C:1]#[N:2])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:20]=[N:19][CH:18]=[N:17]1

참가 물질

6

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 70604082-Cyano-3-fluoropyridine

생성물 1

HCID 218663013-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

To a solution of 2-cyano-3-fluoro-pyridine (2.99 g, 24.49 mmol) in DMF (30 ml) is added cesium carbonate (2.03 g, 29.39 mmol) and 1,2,4-triazole (2.03 g, 29.39 mmol) and the reaction mixture is stirred at 65° C. for 4 h. After cooling to room temperature, the mixture is diluted with water and extracted with EtOAc 3 times. The aqueous layer is saturated with LiCl and further extracted with EtOAc. The combined organic layer is dried on sodium sulfate, concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 2% MeOH containing 10% NH4OH in CH2Cl2 to 6%) to give 3-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile. 1H NMR (CDCl3, 400 MHz) δ8.95 (s, 1H); 8.8 (d, J=4 Hz, 1H); 8.24 (s, 1H); 8.22 (d, J=8.5 Hz, 1H); 7.75 (dd, J=4, 8.5 Hz, 1H).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc 3 times
  3. extractionfurther extracted with EtOAc
  4. customThe combined organic layer is dried on sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography (silica gel, 2% MeOH containing 10% NH4OH in CH2Cl2 to 6%)

출처 및 근거

ORD 기록
ord-f16af703873c4c6dba395327c641ea2f
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610701B2

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