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

HRID 1529333노트

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HRID 1529333 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
23 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-037b6fa5714b45d581134c640fc2e0a3
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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