HCID 69482820, compound → HCID 69483060, compound

HRID 2364218Notes

Reaction equation

HRID 2364218 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]2[CH:11]=[C:12]([N+:20]([O-])=O)[C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]>[Pd].CO>[NH2:20][C:12]1[C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:14][CH:15]=[C:10]([CH2:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[CH:11]=1

Participants

4

Reactant 1

HCID 69482820HCID 69482820, compound

Product 1

HCID 69483060HCID 69483060, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 5-[(3,4-difluorophenyl)methyl]-3-nitro-2-pyridinecarboxylate (1.67 g, 5.42 mmol), 10% Pd-C (1.67 g) and MeOH (170 ml) was reduced under hydrogen for 2 h. The product was filtered through Celite, concentrated in vacuo and purified by chromatography on silica gel, eluting with 50-75% EtOAc/hexanes. The product was triturated with EtOAc to afford an off-white solid collected by filtration. 1H NMR (d6-DMSO) δ 7.77 (1H, s), 7.39-7.30 (2H, m), 7.08-7.05 (1H, m), 6.92 (1H, s), 6.62 (2H, s), 3.88 (2H, s), 3.76 (3H, s); HRMS calcd for C14H12F2N2O2+H+: 279.0945. Found 279.0938.

Workup

  1. filtrationThe product was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography on silica gel
  4. washeluting with 50-75% EtOAc/hexanes
  5. customThe product was triturated with EtOAc
  6. customto afford an off-white solid
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3653ef6d39d14f928f7efc7d58d2ed6f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…