Pyridine → HCID 66758208, compound

HRID 557047Notes

Reaction equation

HRID 557047 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%). ESI-MS m/z: 354 (M+1), UV retention time: 2.88 min.

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-f804659dc1424c9ea2a758fa2d43e4f6
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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