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1,10-Phenanthroline → 6-(2-Fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine

HRID 1401111
ノート
印刷プレビュー

反応式

HRID 1401111 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)(O)[O-].[Na+].Cl[C:35]1[N:40]=[CH:39][C:38]2[N:41]=[C:42]([C:44]3[CH:49]=[C:48]([CH3:50])[C:47]([O:51][CH3:52])=[C:46]([CH3:53])[CH:45]=3)[O:43][C:37]=2[CH:36]=1>CN(C)C=O.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:35]1[N:40]=[CH:39][C:38]2[N:41]=[C:42]([C:44]3[CH:45]=[C:46]([CH3:53])[C:47]([O:51][CH3:52])=[C:48]([CH3:50])[CH:49]=3)[O:43][C:37]=2[CH:36]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 13181,10-PhenanthrolineHCID 97072-FluorophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 717431286-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

生成物 1

HCID 711865366-(2-Fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine
収率 10.6%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
200 °C

実験手順

In a microwaveable vessel, 0.65 g of 6-chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine were dissolved in 12 ml of absolute N,N-dimethylformamide, and 0.25 g of 2-fluorophenol, 0.88 g of cesium carbonate, 21 mg of copper (I) iodide and 40 mg of 1,10-phenanthroline were added. In a microwave reactor, the reaction was heated at 200° C. for 1 h. For work-up, the mixture was added to saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium bisulaite solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by means of preparative HPLC, giving 86 mg (10%) of product.

後処理

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium bisulaite solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-c61f3af7c74e466e89ab391eb6be26e2
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08907093B2

反応ノート

読み込み中…

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