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

HRID 1804827ノート

反応式

HRID 1804827 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2f746194448a418987a24597dc3e76c9
出典データセット
uspto-grants-2013_01
特許番号
US08354432B2

反応ノート

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