Isonicotinic Acid → HCID 8027287, compound

HRID 1056655Notes

Reaction equation

HRID 1056655 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6]N=CC=1.[CH:10]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:29][CH:30]([O:32]C(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:10][O:9][C:1](=[O:8])[CH2:2][C@@H:7]1[CH2:6][CH2:29][CH2:30][O:32]1

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 8027287HCID 8027287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of isonicotinic acid (114.4 g, 0.93 mol), PPh3 (333.2 g, 1.27 mol) and alcohol 3c (110 g, 0.85 mol), in THF (1.1 L) is treated with DIAD (249.5 mL, 1.3 mol) dropwise at 0° C. After stirring for 30 min, the cooling bath is removed and the mixture is stirred at RT for 2 h. The mixture is filtered and then concentrated. The residue is triturated with Et2O and the ether layers are extracted with 30% HCl. The combined aqueous phases are washed with Et2O (2×) and EtOAc (2×) and then neutralized with Na2HPO4 to about pH 6. The neutralized aqueous phase is extracted with Et2O (5×) and then DCM (3×). The combined ether layers are dried (MgSO4) and concentrated in vacuo. The DCM layers are combined and dried (MgSO4), concentrated in vacuo and combined with the product resulting from the ether extractions to afford ester 3d.

Workup

  1. customthe cooling bath is removed
  2. stirringthe mixture is stirred at RT for 2 h
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated
  5. customThe residue is triturated with Et2O
  6. extractionthe ether layers are extracted with 30% HCl
  7. washThe combined aqueous phases are washed with Et2O (2×) and EtOAc (2×)
  8. extractionThe neutralized aqueous phase is extracted with Et2O (5×)
  9. dry with materialThe combined ether layers are dried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated in vacuo
  13. customresulting from the ether extractions

Sources & evidence

ORD record
ord-1c75fb98397b48368554198d84ca80a6
Source dataset
uspto-grants-2016_07
Patent number
US09399645B2

Reaction notes

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