Magnesium → HCID 131732034, compound

HRID 337685Notes

Reaction equation

HRID 337685 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:12]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[Mg]>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:13][C@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 66896027HCID 66896027, compound

Product 1

HCID 131732034HCID 131732034, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a MeOH solution (0.09 M) of 1-(1,1-dimethylethyl) 3-ethyl 3′-{[(methyloxy)methyl]oxy}-5,6-dihydro-4,4′-bipyridine-1,3(2H)-dicarboxylate (1 eq.) from the previous step was added magnesium turnings (3.3 eq.). The suspension was evacuated and back-filled with N2. Finally, the reaction mixture was sonicated at RT for 1.5 h during which the magnesium turnings disappeared. The reaction was then quenched with the addition of EtOAc and 1 N aq. NaOH. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a pale yellow oil.

Workup

  1. customThe suspension was evacuated
  2. additionback-filled with N2
  3. customFinally, the reaction mixture was sonicated at RT for 1.5 h during which the magnesium turnings
  4. customThe reaction was then quenched with the addition of EtOAc and 1 N aq. NaOH
  5. customThe aqueous layer was separated
  6. extractionback-extracted with EtOAc
  7. washThe combined organic extracts were washed further with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-e1373c8153054c1682bc8011597b2fa8
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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