Dichloromethane → 1-Benzenesulfonyl-5-(3,4-dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 1820905노트

반응식

HRID 1820905 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[C:19]([I:20])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)Cl>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+].O>[C:21]1([S:27]([N:17]2[C:14]3=[N:15][CH:16]=[C:11]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:12]=[C:13]3[C:19]([I:20])=[CH:18]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 3

HCID 6344Dichloromethane2회HCID 7369Benzenesulfonyl chlorideHCID 598121695-(3,4-Dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 598119021-Benzenesulfonyl-5-(3,4-dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매2회HCID 14798Sodium Hydroxide용매

실험 절차

Into a Round bottom flask was added 5-(3,4-Dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine, 133, (0.403 g, 0.00106 mol) and Tetra-N-butylammonium bromide (0.0342 g, 0.000106 mol), in 5.000 M of Sodium hydroxide in Water (2.73 mL). Benzenesulfonyl chloride (0.225 g, 0.00127 mol) in Methylene chloride (0.747 mL, 0.0116 mol) was added dropwise. After 2 h, 30 mL of Methylene chloride and 30 mL of water were added. The organic layer was separated and washed with 1M sodium bicarbonate (aq.) (30 ml×2) followed by water (30 ml) and brine (30 mL). The organic layer was collected and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The residue was purified by chromatography (Silica gel, ethyl acetate/hexanes) to give 295 mg of the desired product as a white solid. MS(ESI) [M+H+]+=521.04

후처리

  1. customThe organic layer was separated
  2. washwashed with 1M sodium bicarbonate (aq.) (30 ml×2)
  3. customThe organic layer was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (Silica gel, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-52bd2d1f0d5143619a19d974581fbd5d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605168B2

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