Pyridine → HCID 66779027, compound

HRID 2090960Notes

Reaction equation

HRID 2090960 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][NH:5][N:4]=1)[CH3:2].[CH2:12]([O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)[CH3:13].N1C=CC=CC=1>CN(C)C(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:12]([O:14][C:15]1[CH:20]=[C:19]([N:5]2[CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:3]([CH2:1][CH3:2])=[N:4]2)[CH:18]=[CH:17][CH:16]=1)[CH3:13]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27739203-Ethoxybenzeneboronic acidHCID 178438039HCID 178438039, compound

Product 1

HCID 66779027HCID 66779027, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Methyl 3-ethyl-1H-pyrazole-4-carboxylate (6.9 g) synthesized in Example 39(1) was dissolved in N,N-dimethylacetamide (150 mL), 3-ethoxyphenylboronic acid (15.0 g), copper acetate (16.4 g) and pyridine (14.5 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, 1N hydrochloric acid (70 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 (4.4 g, 36%) as a pale-yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite, 1N hydrochloric acid (70 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-ae55d26ebf43467aabaac720f71e6e04
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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