Water → Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate

HRID 1892564노트

반응식

HRID 1892564 반응식
FC(F)(F)S(O[C:7]1[C:8]([N+:27]([O-:29])=[O:28])=[CH:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[C:12]([C:22](=[O:25])[NH:23][CH3:24])[C:11]=2[CH:26]=1)(=O)=O.[CH3:32][O:33][C:34]1[CH:43]=[CH:42][C:41](B2OC(C)(C)C(C)(C)O2)=[CH:40][C:35]=1[C:36]([O:38][CH3:39])=[O:37].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:14][C:10]3[CH:9]=[C:8]([N+:27]([O-:29])=[O:28])[C:7]([C:41]4[CH:42]=[CH:43][C:34]([O:33][CH3:32])=[C:35]([CH:40]=4)[C:36]([O:38][CH3:39])=[O:37])=[CH:26][C:11]=3[C:12]=2[C:22](=[O:25])[NH:23][CH3:24])=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 22930502Methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 592753912-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl trifluoromethanesulfonate

생성물 1

HCID 67957912Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl trifluoromethanesulfonate (750 mg, 1.622 mmol), methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (569 mg, 1.947 mmol) and cesium carbonate (1057 mg, 3.24 mmol) in dioxane (20 mL)/water (1.0 mL) at rt under nitrogen was added Pd(PPh3)4(0) (187 mg, 0.162 mmol). The reaction mixture was heated to 100° C. and maintained at the same temperature for overnight. The reaction mixture was filtered through celite, and the celite bed washed with ethyl acetate. The filtrate was concentrated and the residue purified by Combiflash using MeOH/CHCl3 as eluant. The desired fraction was collected at 2.5% MeOH in CHCl3. Yield: 0.650 g (83%).

후처리

  1. temperaturemaintained at the same temperature for overnight
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite bed washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue purified by Combiflash
  6. customThe desired fraction was collected at 2.5% MeOH in CHCl3

출처 및 근거

ORD 기록
ord-878e697e8a1e44fa81a9e6815f6c4c73
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507683B2

반응 노트

불러오는 중…