1,10-Phenanthroline → HCID 86675809, 화합물

HRID 59873노트

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HRID 59873 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 86675809HCID 86675809, 화합물수율 33.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
100 °C

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-1ee9304f1fa44a2485a85ac562afe37e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440964B2

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