Pyridine → HCID 22728884, compound

HRID 2085022Notes

Reaction equation

HRID 2085022 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:19][N:18]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][C:17]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]([C:4]2[CH:5]=[CH:6][C:1]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:2][CH:3]=2)[N:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 178469061HCID 178469061, compound

Product 1

HCID 22728884HCID 22728884, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-biphenylboronic acid (1.0 g, 5.1 mmol) and ethyl 3-methylpyrazole-5-carboxylate (0.78 g, 5.1 mmol) in 25 mL dry DCM were added pyridine (1.2 mL, 15 mmol) and anhydrous powder of copper(II) acetate (1.84 g, 10 mmol). Some activated molecular sieve powder was added afterwards. The resulting slurry was refluxed for 2 days under argon. The mixture was diluted with DCM, filtered through celite. The blue filtrate was washed with water (×2), dried, concentrated, purified with flush column to yield ethyl 3-methyl-1-(4-phenylphenyl)-1H-pyrazole-5-carboxylate (26%), Rf 0.67 (1:2 EtOAc: hexane), ES-MS: (M+H)+ 307; and its regioisomer, ethyl 5-methyl-1-(4-phenylphenyl)-1H-pyrazole-3-carboxylate (31%), Rf 0.50 (1:2 EtOAc: hexane), ES-MS: (M+H)+ 307.

Workup

  1. additionSome activated molecular sieve powder was added afterwards
  2. temperatureThe resulting slurry was refluxed for 2 days under argon
  3. filtrationfiltered through celite
  4. washThe blue filtrate was washed with water (×2)
  5. customdried
  6. concentrationconcentrated
  7. custompurified
  8. customwith flush column

Sources & evidence

ORD record
ord-11363da802164dd9a49921e752235a28
Source dataset
uspto-grants-2004_04
Patent number
US06720317B1

Reaction notes

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