Picolinic acid → 1-(2,6-diisopropylphenyl)-2-(3-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-5-methylphenoxy)phenyl)-1H-imidazole

HRID 539455Notes

Reaction equation

HRID 539455 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18]1[CH:19]=[C:20]([OH:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1)([CH3:3])[CH3:2].Br[C:27]1[CH:28]=[C:29]([C:33]2[N:34]([C:38]3[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:41]=[CH:40][C:39]=3[CH:47]([CH3:49])[CH3:48])[CH:35]=[CH:36][N:37]=2)[CH:30]=[CH:31][CH:32]=1.N1C=CC=CC=1C(O)=O.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.CS(C)=O>[CH:44]([C:43]1[CH:42]=[CH:41][CH:40]=[C:39]([CH:47]([CH3:49])[CH3:48])[C:38]=1[N:34]1[CH:35]=[CH:36][N:37]=[C:33]1[C:29]1[CH:28]=[CH:27][CH:32]=[C:31]([O:25][C:20]2[CH:21]=[C:22]([CH3:24])[CH:23]=[C:18]([C:14]3[N:13]([C:5]4[C:6]([CH:10]([CH3:12])[CH3:11])=[CH:7][CH:8]=[CH:9][C:4]=4[CH:1]([CH3:2])[CH3:3])[CH:17]=[CH:16][N:15]=3)[CH:19]=2)[CH:30]=1)([CH3:45])[CH3:46]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 706542932-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazoleHCID 706544253-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-5-methylphenol

Product 1

HCID 706543461-(2,6-diisopropylphenyl)-2-(3-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-5-methylphenoxy)phenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
200 °C

Procedure

To a 300 mL 3-neck round bottom flask was added 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-5-methylphenol (2.5 g, 7.47 mmol), 2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (3.15 g, 8.22 mmol), picolinic acid (1.380 g, 11.21 mmol), copper(I) iodide (0.427 g, 2.242 mmol), potassium phosphate tribasic monohydrate (6.02 g, 26.2 mmol), 100 mL DMSO. Nitrogen was bubbled directly into the mixture and then was heated to 200° C. overnight under nitrogen. The reaction mixture was diluted with ethyl acetate and water and was filtered through Celite. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were washed with 10% LiCl, brine, dried over magnesium sulfate, filtered, and evaporated leaving a residue. The residue was purified by column chromatography eluting with 40 and 50% ethyl acetate/hexane (1.95 g, 41%).

Workup

  1. customNitrogen was bubbled directly into the mixture
  2. additionThe reaction mixture was diluted with ethyl acetate and water
  3. filtrationwas filtered through Celite
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe organic layers were washed with 10% LiCl, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customleaving a residue
  11. customThe residue was purified by column chromatography
  12. washeluting with 40 and 50% ethyl acetate/hexane (1.95 g, 41%)

Sources & evidence

ORD record
ord-d47b5d3470494e4d8cdd487ce2c233f3
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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