Potassium Carbonate → HCID 57749789, compound

HRID 2266744Notes

Reaction equation

HRID 2266744 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6](I)[CH:5]=1.[CH:19]([C:22]1[NH:23][CH:24]=[CH:25][N:26]=1)([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O.[Cu]I>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([N:23]2[CH:24]=[CH:25][N:26]=[C:22]2[CH:19]([CH3:21])[CH3:20])[CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 594325793-Iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Product 1

HCID 57749789HCID 57749789, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (500 mg, 1.42 mmol) in DMSO (10 ml) was added 2-Isopropylimidazole (312 mg, 2.83 mmol), CuI (54 mg, 0.283 mmol), N,N′-dimethylglycine HCl salt (79 mg, 0.567 mmol) and K2CO3 (391 mg, 2.83 mmol) under N2 atmosphere. The mixture was heated to 100° C. overnight. After cooling to room temperature, the mixture was diluted with H2O (15 ml). The mixture was extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (30%-75% EtOAc in hexanes) to afford 3-(2-isopropyl-imidazol-1-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester as an off-white solid (270 mg, 57%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by flash chromatography (30%-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fcb93548b2eb436895f69de6ebe84ed2
Source dataset
uspto-grants-2010_12
Patent number
US07858654B2

Reaction notes

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