Pyridine → HCID 53419305, compound

HRID 714627Notes

Reaction equation

HRID 714627 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 53419305HCID 53419305, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

400 mg (2.85 mmol) of ethyl 1H-pyrazole-4-carboxylate, 893 mg (5.71 mmol) of 2-chlorophenyl-boronic acid, 100 mg of 3 Å molecular sieve and 778 mg (4.28 mmol) of copper(II) acetate were initially charged in 2 ml of dichloromethane, and 461 μl (5.71 mmol) of pyridine were added. The mixture was stirred at RT for 20 h. For work-up, the mixture was filtered through a little kieselguhr, the filter residue was rinsed with about 10 ml of dichloromethane and the combined filtrates were concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 5:1). This gave 71 mg (10% of theory) of the target compound.

Workup

  1. filtrationFor work-up, the mixture was filtered through a little kieselguhr
  2. washthe filter residue was rinsed with about 10 ml of dichloromethane
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel (mobile phase

Sources & evidence

ORD record
ord-598422a68f11414c933f0b7def85b126
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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