Cesium carbonate → 3-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methoxybenzoic acid

HRID 555107노트

반응식

HRID 555107 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[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.B([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[C:35]([OH:37])=[O:36])(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:14][C:10]3[CH:9]=[CH:8][C:7]([C:32]4[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=4[O:41][CH3:42])[C:35]([OH:37])=[O:36])=[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 10796Cesium carbonateHCID 312751,4-DioxaneHCID 426145415-Carboxy-2-methoxybenzeneboronic acidHCID 59275663(4-Fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate

생성물 1

HCID 592757493-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methoxybenzoic acid

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

To a 150 mL sealed tube was added 2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate (1.252 g, 3 mmol), 3-borono-4-methoxybenzoic acid (0.882 g, 4.50 mmol), cesium carbonate (1.466 g, 4.50 mmol), tetrakis(triphenyl phosphine)palladium(0) (0.069 g, 0.060 mmol), dioxane (18 mL) and water (3.60 mL). The vial was sealed and heated in an oil bath over night at 85° C. The reaction mixture was then filtered through CELITE® and concentrated in vacuo. Cold 0.5N HCl was then added and the heterogeneous mixture was stirred for 30 minutes. The resulting product, a white solid was filtered, washed with water and dried overnight to give a quantitative yield of 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methoxy benzoic acid which was carried on without further purification. LCMS m/z 420.88 (M+H), Rt 2.002 min., 88% purity.

후처리

  1. customTo a 150 mL sealed tube
  2. customThe vial was sealed
  3. filtrationThe reaction mixture was then filtered through CELITE®
  4. concentrationconcentrated in vacuo
  5. additionCold 0.5N HCl was then added
  6. filtrationThe resulting product, a white solid was filtered
  7. washwashed with water
  8. customdried overnight

출처 및 근거

ORD 기록
ord-292413355f5740309216050d9303469b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048887B2

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