Chlorosuccinimide → 2-(4-chloro-5-methyl-1H-pyrazol-3-yl)pyridine

HRID 1804827노트

반응식

HRID 1804827 반응식
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:3]=1.[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:5][NH:6][C:2]=1[CH3:1]

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 27555682-(5-methyl-1H-pyrazol-3-yl)pyridine

생성물 1

HCID 578402932-(4-chloro-5-methyl-1H-pyrazol-3-yl)pyridine수율 53%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

Preparation 2: A solution of 2-(5-methyl-1H-pyrazol-3-yl)pyridine (500 mg, 3.15 mmol) in acetonitrile (912 mL) was treated with N-chlorosuccinimide in 6 portions and the resulting mixture stirred at 70° C. for 14 h. The mixture was cooled and then concentrated in vacuo to yield a residue. The residue was partitioned between EtOAc (8 mL) and H2O (3 mL). The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to yield a residue. The residue was purified by flash chromatography on silica gel using 20-80% EtOAc in hexanes to give the title compound (300 mg, 53%).

후처리

  1. customPreparation 2
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customto yield a residue
  5. customThe residue was partitioned between EtOAc (8 mL) and H2O (3 mL)
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto yield a residue
  10. customThe residue was purified by flash chromatography on silica gel using 20-80% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-2f746194448a418987a24597dc3e76c9
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354432B2

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