Pyridine → HCID 66777713, compound

HRID 2090938Notes

Reaction equation

HRID 2090938 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:5][CH:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.N1C=CC=CC=1>CN(C)C(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:5]2[CH:6]=[C:2]([CH3:1])[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4]2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 178470484HCID 178470484, compound

Product 1

HCID 66777713HCID 66777713, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Ethyl 4-methyl-1H-pyrazole-3-carboxylate (2.58 g) was dissolved in N,N-dimethylacetamide (50 mL), 4-methoxyphenylboronic acid (5.0 g), copper acetate (6.0°g) and pyridine (5.3 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL) was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (2.7 g, 66%) as a pale-yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL)
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

Sources & evidence

ORD record
ord-6dd3f7b026914665b83894d49ed7b547
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…