Potassium Carbonate → 1-(3-Methoxy-2-nitro-phenyl)-4-methyl-2-o-tolyl-1H-imidazole

HRID 254327Notes

Reaction equation

HRID 254327 reaction equation
Br[C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=2[N+:16]([O-:18])=[O:17])[CH:4]=[C:5]([CH3:7])[N:6]=1.[C:19]1([CH3:34])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1OB(C1C=CC=CC=1)O.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:15][O:14][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[C:8]([N:3]2[CH:4]=[C:5]([CH3:7])[N:6]=[C:2]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH3:34])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 577324682-Bromo-1-(3-methoxy-2-nitro-phenyl)-4-methyl-1H-imidazoleHCID 66861927(2-Methylphenoxy)-phenylborinic acid

Product 1

HCID 577324501-(3-Methoxy-2-nitro-phenyl)-4-methyl-2-o-tolyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

Intermediate 1D, method D (0.6 g, 1.9 mmol) and O-tolyl phenyl boronic acid (0.56 g, 3.8 mmol) were dissolved in a solution containing 1,4-dioxane (16 mL) and water (4 mL). To this was then added potassium carbonate (0.56 g, 3.8 mmol). Argon was bubbled into the reaction for 3 min and (triphenylphosphine) palladium (0) (0.1 g, 5% mol) added. The reaction was sealed then heated to 115° C. for 16 hrs, poured into water and extracted with ethyl acetate. The organic layer was separated and washed with water then brined, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and the crude purified by flash chromatography on silica gel in 10:1 ethyl acetate/methylene chloride. A white solid (0.5 g) was recovered. MS (ES) m/z 324.1 [M+1]+

Workup

  1. customArgon was bubbled into the reaction for 3 min
  2. addition(triphenylphosphine) palladium (0) (0.1 g, 5% mol) added
  3. customThe reaction was sealed
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe solvent was removed under reduced pressure
  11. customthe crude purified by flash chromatography on silica gel in 10:1 ethyl acetate/methylene chloride
  12. customA white solid (0.5 g) was recovered

Sources & evidence

ORD record
ord-7143be45a40c430cac964f77fb583618
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

Loading…