Methyl iodide → 1-Bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

HRID 409284노트

반응식

HRID 409284 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:23])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4].IC.[C:26](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:23])[C:8]2[C:13]([C:14]=1[O:15][CH3:26])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:4]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866170621-Bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

생성물 1

HCID 866170821-Bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester수율 52.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
45 °C

실험 절차

A mixture of 1-bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.89 g, 5.07 mmol), iodomethane (632 μL, 10.13 mmol), cesium carbonate (3.3 g, 10.13 mmol) and dimethylformamide (15 mL) was stirred at 45° C. for sixteen hours before it was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow solid (1.03 g): MS: (+) m/z 387.64, 389.75 (M+1, 79Br/81Br).

후처리

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-99305207843d4744bbd011ae42858c48
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759373B2

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