Sodium Iodide → 1-(4-Iodo-pyrazolo[3,4-b]pyridin-1-yl)ethanone

HRID 724437ノート

反応式

HRID 724437 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[I-:11].[Na+].[C:13](Cl)(=[O:15])[CH3:14].OS([O-])=O.[Na+]>C(#N)C>[I:11][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:13](=[O:15])[CH3:14])[N:9]=[CH:10][C:3]=12

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 3100454-Chloro-1H-pyrazolo[3,4-b]pyridineHCID 23665763Sodium Bisulfite

生成物 1

HCID 218774001-(4-Iodo-pyrazolo[3,4-b]pyridin-1-yl)ethanone収率 42%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-chloro-1H-pyrazolo[3,4-b]pyridine (820 mg, 5.30 mmol), sodium iodide (2.4 mg, 16.0 mmol), and acetyl chloride (0.8 ml) in acetonitrile (6 ml) was refluxed 8 h. The mixture was then treated with a 10% aqueous solution of NaCO3 (10 ml), and a 10% aqueous solution of NaHSO3 (10 ml), and held 10 min. The mixture was extracted with ethyl acetate (50 ml), and the organics were washed with brine (10 ml), dried over MgSO4, and evaporated under reduced pressure. Purification by silica gel chromatography gave 1-(4-iodo-pyrazolo[3,4-b]pyridin-1-yl)-ethanone as a brown solid (650 mg, 42%). 1H NMR (300 MHz, CDCl3) δ 8.39 (d, 1H, J=5.0 Hz), 8.04 (s, 1H), 7.76 (d, 1H, J=5.0 Hz), 2.88 (s, 3H).

後処理

  1. temperaturewas refluxed 8 h
  2. extractionThe mixture was extracted with ethyl acetate (50 ml)
  3. washthe organics were washed with brine (10 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-5c5e4f82afa14fedaf5fb02f98d54cdd
出典データセット
uspto-grants-2006_11
特許番号
US07141587B2

反応ノート

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