1,10-Phenanthroline → HCID 86675809、化合物

HRID 59873ノート

反応式

HRID 59873 の反応式
[F:1][C:2]([F:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[N:17][N:18]=2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].I[C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.[Cu]I>[F:19][C:2]([F:1])([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:15][C:16]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)=[N:17][N:18]=2)=[CH:12][CH:13]=1)[C:3]([F:6])([F:5])[F:4]

参加物

8

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 69273Methyl 4-iodobenzoateHCID 866758082-(4-(Perfluoroethoxy)phenyl)-1,3,4-oxadiazole

生成物 1

HCID 86675809HCID 86675809、化合物収率 33.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazole (2.186 g, 7.80 mmol), methyl 4-iodobenzoate (3.07 g, 11.70 mmol), copper(I) iodide (0.28 g, 1.47 mmol), 1,10-phenanthroline (0.30 g, 1.67 mmol), and cesium carbonate (2.54 g, 7.80 mmol) in anhydrous DMSO (20 mL) was heated at 100° C. for 18 hours. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were dried over anhydrous sodium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-50% EtOAc/hexanes) provided methyl 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoate as a white solid (1.08 g, 33%): mp 185-191° C.; 1H NMR (400 MHz, CDCl3) δ 8.25-8.19 (m, 6H), 7.41 (t, J=9.4 Hz, 2H), 3.98 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −85.96, −85.98, −87.79; ESIMS m/z 415 ([M+H]+).

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted three times with EtOAc
  3. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customPurification by flash chromatography (0-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1ee9304f1fa44a2485a85ac562afe37e
出典データセット
uspto-grants-2016_09
特許番号
US09440964B2

反応ノート

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