Pyridine → HCID 66779018, compound

HRID 2090929Notes

Reaction equation

HRID 2090929 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][NH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.N1C=CC=CC=1>CN(C)C(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:11][C:12]1[CH:17]=[C:16]([N:4]2[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:2]([CH3:1])=[N:3]2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2734323(3-Chlorophenyl)boronic acidHCID 178498883HCID 178498883, compound

Product 1

HCID 66779018HCID 66779018, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Methyl 3-methyl-1H-pyrazole-4-carboxylate (1.6 g) synthesized in Example 1(3) was dissolved in N,N-dimethylacetamide (30 mL), 3-chlorophenylboronic acid (3.58 g), copper acetate (5.0 g) and pyridine (4.0 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=1:4, volume ratio) to give the title object compound (1.9 g, 67%) 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=1:4, volume ratio)

Sources & evidence

ORD record
ord-7d4f890831a946ada04be2964f90c0e4
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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