Pyridine → HCID 12595218, compound

HRID 2090853Notes

Reaction equation

HRID 2090853 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][NH:4][N:3]=1.[CH:11]1(C(C2C(CCC3C=CC=CC=3)=NN(C3C=CC=CC=3)C=2)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(B(O)O)C=CC=CC=1.N1C=CC=CC=1>CC(N(C)C)=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 66776943HCID 66776943, compoundHCID 178498883HCID 178498883, compound

Product 1

HCID 12595218HCID 12595218, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

Methyl 3-methyl-1H-pyrazole-4-carboxylate (14.4 g) synthesized in Example 1, (3) was dissolved in dimethylacetamide (200 mL), phenylboronic acid (25.0 g), copper acetate (36.4 g) and pyridine (32 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, 1N hydrochloric acid (100 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=10:1, volume ratio) to give the title object compound (11.4 g, 53%) as a pale-yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite, 1N hydrochloric acid (100 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=10:1, volume ratio)

Sources & evidence

ORD record
ord-65410d62d1774ccd9d9cf9969a9e1705
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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