Cesium carbonate → 4-[2-[5-(2-Methoxy-phenyl)-pyridin-2-yloxy]-acetylamino]-thiophene-3-carboxylic acid methyl ester

HRID 14596

반응식

HRID 14596 반응식
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:21])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][N:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:21])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[O:23][CH3:22])=[CH:16][N:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4]

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 27339582-Methoxyphenylboronic acidHCID 686917104-[2-(5-Bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

생성물 1

HCID 686883444-[2-[5-(2-Methoxy-phenyl)-pyridin-2-yloxy]-acetylamino]-thiophene-3-carboxylic acid methyl ester수율 79%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of 4-[2-(5-bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (50 g, 0.135 mmol) in a mixture of tetrahydrofuran (10.5 mL) and water (2.5 mL) was added 2-methoxyphenylboronic acid (24.5 mg, 0.162 mmol) and cesium carbonate (175.3 mg, 0.54 mmol). The solution was then degassed by bubbling a flux of argon for 20 minutes before adding tetrakis(triphenylphosphine)palladium (4.24 mg, 0.0034 mmol). The reaction mixture was then stirred overnight at 80° C. under argon atmosphere before allowing to cool down to room temperature and diluting with ethyl acetate. The reaction mixture was then filtered; the filtrate was then washed twice with water and dried over sodium sulfate before being concentrated in vacuo. The residue was then purified by column chromatography (SiO2, EtOAc/Heptane, 0-60%) to yield the title compound as a light yellow solid (42.5 mg, 79%).

후처리

  1. customThe solution was then degassed
  2. customby bubbling a flux of argon for 20 minutes
  3. temperatureto cool down to room temperature
  4. filtrationThe reaction mixture was then filtered
  5. washthe filtrate was then washed twice with water
  6. dry with materialdried over sodium sulfate
  7. concentrationbefore being concentrated in vacuo
  8. customThe residue was then purified by column chromatography (SiO2, EtOAc/Heptane, 0-60%)

출처 및 근거

ORD 기록
ord-2a59fa4fb2cf49b090f85b7fa8e139dc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732452B2

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