Indoline → HCID 18629224, 화합물

HRID 1271152노트

반응식

HRID 1271152 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br-:10].[Br-:11].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:10][C:6]1[CH:5]=[C:4]2[C:9](=[C:8]([Br:11])[CH:7]=1)[NH:1][CH2:2][CH2:3]2

참가 물질

4

반응물 2

HCID 10328IndolineHCID 21124087Pyridiniumtribromide

생성물 1

HCID 18629224HCID 18629224, 화합물수율 84.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Part A: Indoline (2.2 g, 18.04 mmol), dissolved in dichloromethane (160 mL) was stirred with pyridinium tribromide (12 g, 37.6 mmol) for 16 h at 25° C. The reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL). The dichloromethane was separated, dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent to give 5,7-dibromoindoline (4.2 g, 84% yield). 1H NMR(CDCl3) δ 7.28 (m, 1H), 7.11 (s, 1H), 3.96 (s br, 1H ), 3.63 (t J=9 Hz, 1H), 3.13 (t J=9 Hz, 2H).

후처리

  1. customThe reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL)
  2. customThe dichloromethane was separated
  3. dry with materialdried (MgSO4)
  4. customThe residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent

출처 및 근거

ORD 기록
ord-76f19e53dee44d659a2d4af7c775bd0e
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205306B2

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