Cesium carbonate → 5-(4-Methanesulfonyl-phenoxy)-2-methyl-benzofuran-7-carboxylic acid methyl ester

HRID 1643545

반응식

HRID 1643545 반응식
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][S:8]([C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[CH3:18][O:19][C:20]([C:22]1[C:30]2[O:29][C:28]([CH3:31])=[CH:27][C:26]=2[CH:25]=[C:24]([OH:32])[CH:23]=1)=[O:21]>CN(C=O)C>[CH3:18][O:19][C:20]([C:22]1[C:30]2[O:29][C:28]([CH3:31])=[CH:27][C:26]=2[CH:25]=[C:24]([O:32][C:14]2[CH:15]=[CH:16][C:11]([S:8]([CH3:7])(=[O:10])=[O:9])=[CH:12][CH:13]=2)[CH:23]=1)=[O:21]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 595603415-Hydroxy-2-methyl-benzofuran-7-carboxylic acid methyl ester

생성물 1

HCID 595603235-(4-Methanesulfonyl-phenoxy)-2-methyl-benzofuran-7-carboxylic acid methyl ester수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

Cs2CO3 (2.36 g, 7.24 mmol) and 4-flurophenyl methyl sulfone (631 mg, 3.62 mmol) were added to a solution of 5-hydroxy-2-methyl-benzofuran-7-carboxylic acid methyl ester (4d) (746 mg, 3.62 mmol) in DMF (5 mL). The mixture was heated to 120° C. overnight and then cooled to RT. The mixture was then quenched with H2O (80 mL) and extracted with EtOAc 92×100 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 4% CH3OH/CH2Cl2 to afford brown color oil (1.2 g, 92%). 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 2 H) 7.86-7.90 (m, 1 H) 7.58 (d, J=2.53 Hz, 1 H) 7.38 (d, J=2.53 Hz, 1 H) 7.05 (d, J=8.84 Hz, 1 H) 6.44 (s, 1H) 3.99 (s, 3 H) 3.05 (s, 3 H) 2.56 (s, 3 H); LCMS for C18H16O6S m/z 361.00 (M+H)+.

후처리

  1. temperaturecooled to RT
  2. customThe mixture was then quenched with H2O (80 mL)
  3. extractionextracted with EtOAc 92×100 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph
  7. washeluting with 4% CH3OH/CH2Cl2

출처 및 근거

ORD 기록
ord-15e71aa9e627400ea65488bd1924fd73
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119624B2

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