Imidazole → HCID 59504680, compound

HRID 2400587Notes

Reaction equation

HRID 2400587 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.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Cu+].O.CN(C=O)C>[N:27]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:12]=[C:11]([C:13]4[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]5[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=5)[N:14]=4)[O:10][N:9]=3)=[CH:4][CH:3]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

10

Reactant 5

HCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 25118340HCID 25118340, compound

Product 1

HCID 59504680HCID 59504680, compound

Reagents, catalysts & solvents 4

HCID 9813164Copper(I) trifluoromethanesulfonateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-(4-iodophenyl)-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Example 13, 250 mg, 0.548 mmol), imidazole (56 mg, 0.822 mmol), caesium carbonate (197 mg, 0.603 mmol), copper-(I) trifluoromethanesulfonate (15 mg; 0.027 mmol), dibenzylideneacetone (6.7 mg, 0.027 mmol) and 1,10-phenanthroline (99 mg, 0.548 mmol) in toluene (1 mL) was heated to reflux under an inert atmosphere of argon over night. In order to increase solubility, DMF (100 μL) was added, and stirring was continued at 120° C. for 24 h. After being cooled to rt, water (5 mL) was added and the product was extracted with ethyl acetate. After the organic extract had been washed with brine and dried over anhydrous magnesium sulfate, it was filtered and concentrated in vacuo. The residue was subjected to preparative HPLC to afford the title compound in pure form (20 mg, 9%): 1H NMR (400 MHz, CDCl3) 8.33 (d, 2H), 7.98 (broad s, 1H), 7.53 (d, 2H), 7.38 (broad s, 1H), 7.26 (broad s, 1H, partially obscured by CHCl3 signal), 7.14 (d, 2H), 7.08 (d, 2H), 6.81 (s, 1H), 5.41 (s, 2H), 2.32 (s, 3H), 2.28 (s, 3H); ES-MS m/z 397, HPLC RT (Method K) 1.06 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under an inert atmosphere of argon over night
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate
  5. extractionAfter the organic extract
  6. washhad been washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate, it
  8. filtrationwas filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa4112ba1a7f4284ba49edefcf991e8f
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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