1H-1,2,4-Triazole → 5-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 857772노트

반응식

HRID 857772 반응식
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:10][C:7]1[CH:8]=[CH:9][C:2]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 1235582,5-Difluorobenzonitrile

생성물 1

HCID 218662545-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2,5-difluorobenzonitrile (500 mg, 3.6 mmol), 1,2,4-triazole (273 mg, 3.9 mmol) and Cs2CO3 (1.27 g, 3.9 mmol) in DMF (10 mL) was heated at 80° C. for 2 days. The solvent was removed under reduced pressure. The residue was partitioned between H2O and EtOAc. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as an off white solid (596 mg) along with a minor bis-alkylated byproduct. 1H NMR (400 MHz, CDCl3): δ 8.71 (s, 1H), 8.19 (s, 1H), 7.75–7.98 (m, 1H), 7.48–7.57 (m, 2H).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between H2O and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-85d679a2c08b4794b50c68c1f33398c9
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144899B2

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