1,10-Phenanthroline → HCID 86675809, compound

HRID 59873Notes

Reaction equation

HRID 59873 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 86675809HCID 86675809, compoundYield 33.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

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]+).

Workup

  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)

Sources & evidence

ORD record
ord-1ee9304f1fa44a2485a85ac562afe37e
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

Loading…