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

HRID 2075246ノート

反応式

HRID 2075246 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e28a09ac00148fd91dd9bcc38ff6797
出典データセット
uspto-grants-2011_04
特許番号
US07919519B2

反応ノート

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