Picolinic acid → HCID 70654242, compound

HRID 539468Notes

Reaction equation

HRID 539468 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.I[C:21]1[CH:22]=[C:23]([C:27]2[N:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[CH:29]=[CH:30][N:31]=2)[CH:24]=[CH:25][CH:26]=1.N1C=CC=CC=1C(O)=O.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.CS(C)=O>[O:18]([C:25]1[CH:24]=[C:23]([C:27]2[N:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[CH:29]=[CH:30][N:31]=2)[CH:22]=[CH:21][CH:26]=1)[C:14]1[CH:13]=[C:12]([C:8]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:19])[CH:11]=[CH:10][N:9]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 70654404HCID 70654404, compoundHCID 70654448HCID 70654448, compound

Product 1

HCID 70654242HCID 70654242, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

To a 250 mL round bottom flask was added 3-(1-(o-tolyl)-1H-imidazol-2-yl)phenol (2.009 g, 8.03 mmol), 2-(3-iodophenyl)-1-(o-tolyl)-1H-imidazole (3.18 g, 8.83 mmol), picolinic acid (1.482 g, 12.04 mmol), copper(I) iodide (0.459 g, 2.408 mmol), potassium phosphate tribasic monohydrate (6.47 g, 28.1 mmol), and 80 mL DMSO. Nitrogen was bubbled directly into the mixture and then was heated to 150° C. overnight under nitrogen. The reaction mixture was cooled to room temperature, added water, extracted twice with ethyl acetate, dried extracts over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography eluting with 80% ethyl acetate/hexane (2.12 g, 55%).

Workup

  1. customNitrogen was bubbled directly into the mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionadded water
  4. extractionextracted twice with ethyl acetate
  5. dry with materialdried extracts over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. washeluting with 80% ethyl acetate/hexane (2.12 g, 55%)

Sources & evidence

ORD record
ord-f18e17060df54968a78d447b403dfd50
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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