N-Iodosuccinimide → 5-(2,6-difluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine

HRID 1529333ノート

反応式

HRID 1529333 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]2[CH:15]=[CH:16][NH:17][C:12]2=[CH:11][CH:10]=1.C1C(=O)N([I:25])C(=O)C1>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]2[C:15]([I:25])=[CH:16][NH:17][C:12]2=[CH:11][CH:10]=1

参加物

5

反応物 2

HCID 120273N-IodosuccinimideHCID 679601495-(2,6-difluorophenyl)-1H-pyrrolo[3,2-b]pyridine

生成物 1

HCID 679598505-(2,6-difluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine収率 78%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
23 °C

実験手順

A solution of 5-(2,6-difluorophenyl)-1H-pyrrolo[3,2-b]pyridine (700 mg, 3.04 mmol) in THF (25 mL) was treated with n-iodosuccinimide (753 mg, 3.34 mmol, Alfa-Aesar). The reaction was stirred at 23° C. under N2. After 30 min, the solution was diluted with EtOAc (250 ml) and washed with brine (175 ml), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 15-40% EtOAc/hexane), affording 5-(2,6-difluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine (255 mg, 78%). MS (ESI, pos. ion) m/z: 356.9 (M+1).

後処理

  1. washwashed with brine (175 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography (eluent: 15-40% EtOAc/hexane)

出典と根拠

ORDレコード
ord-037b6fa5714b45d581134c640fc2e0a3
出典データセット
uspto-grants-2015_07
特許番号
US09090593B2

反応ノート

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