1,2-Dibromoethane → HCID 69552004, 화합물

HRID 1833174노트

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HRID 1833174 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[C:9]([C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH3:29])[CH3:28])[CH:21]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:37][CH2:38][CH2:39]Br.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:16][CH2:39][CH2:38][Br:37])[CH:14]=2)[C:9]([C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH3:29])[CH3:28])[CH:21]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 136334117HCID 136334117, 화합물

생성물 1

HCID 69552004HCID 69552004, 화합물수율 75.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

To a stirred solution of 6-hydroxy-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester (73 mg, 0.18 mmol) in N,N dimethylformamide (2 mL) was added potassium carbonate (197 mg, 1.42 mmol) and 1,2-dibromoethane (0.046 mL, 0.89 mmol) at room temperature. The reaction mixture was heated 85° C. for 2 hrs. The solvent was evaporated and the crude product was diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 30% ethyl acetate/hexane) afforded 6-(2-bromo-ethoxy)-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester as a white solid (70 mg, 75% yield).

후처리

  1. customThe solvent was evaporated
  2. additionthe crude product was diluted with ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0a2e8794a064488fa5c11c9bf67b28a1
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067529B2

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