Pyridine → HCID 66758208, compound

HRID 242655Notes

Reaction equation

HRID 242655 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.COC([CH:15]1[CH2:20][NH:19][CH2:18][CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:24][O:23][C:21]([CH:18]1[N:19]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:20][CH2:15][N:16]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17]1)=[O:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 742994-Chlorophenylboronic acidHCID 27568181-(1,1-Dimethylethyl) 2-methyl 1,2-piperazinedicarboxylate

Product 1

HCID 66758208HCID 66758208, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Chloro phenyl boronic acid (2.0 equiv, 3.68 mmol) and piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1.0 equiv, 1.84 mmol) were dissolved in dichloromethane followed by the addition of copper acetate (1.0 equiv), 4 Å molecular sieves and pyridine (2.0 equiv). The reaction mixture was stirred at room temperature for 72 h. The reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, filtered through celite and concentrated. The crude product was purified using gradient elution from hexane/ethyl acetate (5%) to hexane/ethyl acetate (20%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customThe crude product was purified
  6. washelution from hexane/ethyl acetate (5%) to hexane/ethyl acetate (20%)

Sources & evidence

ORD record
ord-4ee769c5d3da4e1283aaa9f85dc22b27
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

Loading…