Nitrogen → HCID 58579956, compound

HRID 389260Notes

Reaction equation

HRID 389260 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:14]2[C:19]([C:20]#[N:21])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:7]=1)C.N#N>CO.Cl.[Pd]>[CH3:1][O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:14]2[C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 947NitrogenHCID 58579970HCID 58579970, compound

Product 1

HCID 58579956HCID 58579956, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

[3-(3-Cyano-pyridin-2-yl)-4-methoxy-phenyl]-acetic acid ethyl ester (0.579 g, 2.0 mmol) was dissolved in MeOH (20 mL) and 12N aqueous HCl (4 mL). After the mixture was purged with N2, 10% palladium on carbon (50 wt % w/w; 0.300 g, 0.15 mmol) was added, and the reaction was stirred overnight under 55 psi of H2 using a Parr shaker. After stirring for 18 hours, the mixture was filtered and neutralized with 1N aqueous NaOH (50 mL), and then concentrated to remove MeOH. The residue was partitioned between EtOAc and H20, and the organic layer was separated and washed five times with water. The organic layer was dried, filtered, and concentrated to give the title compound.

Workup

  1. additionwas added
  2. stirringAfter stirring for 18 hours
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customto remove MeOH
  6. customThe residue was partitioned between EtOAc and H20
  7. customthe organic layer was separated
  8. washwashed five times with water
  9. customThe organic layer was dried
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-73821c8d445340cc93bf5e7649305e4e
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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