1,10-Phenanthroline → 4-(6-Benzylbenzo[d]oxazol-2-yl)-3-fluorobenzaldehyde

HRID 2075246노트

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HRID 2075246 반응식
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21]([C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:45])[C:36]2[CH:41]=[CH:40][C:39]([CH:42]=[O:43])=[CH:38][C:37]=2[F:44])=[C:30](I)[CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[CH2:21]([C:28]1[CH:33]=[CH:32][C:31]2[N:34]=[C:35]([C:36]3[CH:41]=[CH:40][C:39]([CH:42]=[O:43])=[CH:38][C:37]=3[F:44])[O:45][C:30]=2[CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 59651840N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide

생성물 1

HCID 584152734-(6-Benzylbenzo[d]oxazol-2-yl)-3-fluorobenzaldehyde

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

1,10-Phenanthroline (0.016 g, 0.087 mmol), cuprous iodide (0.008 g, 0.044 mmol), cesium carbonate (0.21 g, 0.65 mmol), and N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide (0.200 g, 0.44 mmol) were combined under argon. Dioxane (2 mL) was added and the reaction was sealed and heated to 90° C. for 24 h. The reaction was cooled and partitioned between EtOAc and water. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by ISCO, 40 g, 0-30% EtOAc/hexanes to give 4-(6-benzylbenzo[d]oxazol-2-yl)-3-fluorobenzaldehyde as a white solid. MS (ESI) m/z: Calculated: 331.1; Observed: 332.1 (M++1).

후처리

  1. customthe reaction was sealed
  2. temperatureThe reaction was cooled
  3. custompartitioned between EtOAc and water
  4. washThe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by ISCO, 40 g, 0-30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-1e28a09ac00148fd91dd9bcc38ff6797
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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