1,10-Phenanthroline → HCID 25118343, compound

HRID 2400570Notes

Reaction equation

HRID 2400570 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)[N:14]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:27][CH:28]([OH:30])[CH3:29].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I.C(OCC)(=O)C.O>[CH:28]([O:30][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)[N:14]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1)([CH3:29])[CH3:27]

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 3776IsopropanolHCID 10796Cesium carbonateHCID 25118340HCID 25118340, compound

Product 1

HCID 25118343HCID 25118343, compoundYield 17.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-iodophenyl)-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Example 13, 200 mg, 0.44 mmol), 2-propanol (1 ml, 13.06 mmol), copper(I) iodide (8.4 mg, 0.04 mmol), phenanthroline (16 mg, 0.09 mmol) and cesium carbonate (286 mg, 0.88 mmol) was stirred at 100° C. for five hours in a microwave reactor (CEM Discover). The reaction mixture was cooled and water (50 mL) and ethyl acetate (50 mL) was added. The layers were separated and the organic layer was washed with water and brine and then dried with magnesium sulfate. The solvent was evaporated and the residue was purified using preparative HPLC to afford the title compound as a white solid (30 mg, 16%): 1H NMR (400 MHz, CDCl3) 8.12 (d, 2H), 7.13 (d, 2H), 7.07 (d, 2H), 6.97 (d, 2H), 6.79 (s, 1H), 5.41 (s, 2H), 4.63 (sept, 1H), 2.33 (s, 3H), 2.26 (s, 3H), 1.38 (d, 6H); ES-MS m/z 389 (MH)+, HPLC RT (Method E) 2.67 min.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe layers were separated
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified

Sources & evidence

ORD record
ord-7c07fc0a361140f381e73a16369a478a
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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