N-Iodosuccinimide → 2-Chloro-3-iodopyrazolo[1,5-A]pyridine

HRID 530015ノート

反応式

HRID 530015 の反応式
[Cl:1][C:2]1[CH:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[I:11]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[C:10]([I:11])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 122844332-Chloropyrazolo[1,5-a]pyridine

生成物 1

HCID 717433402-Chloro-3-iodopyrazolo[1,5-A]pyridine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-chloro-pyrazolo[1,5-a]pyridine (0.500 g, 3.28 mmol) in acetonitrile (16.4 mL) was added N-iodosuccinimide (0.885 g, 3.93 mmol). The resulting mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound. LCMS m/z 278.72 [M+H]+, 280.64 [M+2+H]+, 1H NMR (500 MHz, CDCl3) 8.35 (d, J=6.8 Hz, 1 H), 7.38 (d, J=9.0 Hz, 1H), 7.24 (d, J=8.6 Hz, 1 H), 6.84-6.81 (m, 1 H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-7895939d8b494ae0b01a25432ada00a1
出典データセット
uspto-grants-2016_05
特許番号
US09351973B2

反応ノート

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