HCID 58886132, compound → HCID 58886610, compound

HRID 425895Notes

Reaction equation

HRID 425895 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH2:24])=[C:14]([O:16]CC3C=CC=CC=3)[CH:15]=2)=[CH:6][CH:5]=1>CCO.O.[Pd]>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH2:24])=[C:14]([OH:16])[CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 58886132HCID 58886132, compound

Product 1

HCID 58886610HCID 58886610, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

To a stirring solution of 4-(6-amino-5-benzyloxy-pyridin-3-yl)-benzoic acid methyl ester (10.0 g, 0.03 mol) in EtOH:H2O (95:5, 600 mL) was added Pd/C (15.9 g, 0.015 mol) (the reaction was de-gassed under vacuum). The solution was allowed to stir under an H2 atmosphere for 22 hr. The solution was filtered through wet celite and the celite washed with EtOH. The filtrate was concentrated under vacuum to yield 4-(6-Amino-5-hydroxy-pyridin-3-yl)-benzoic acid methyl ester (2.3 g, 9.3 mmol, 31%). 1H NMR (MeOD, 300 MHz) δ 3.90 (s, 3H), 7.21 (d, 1H, J, 1.9 Hz), 7.62 (d, 2H, J, 8.5 Hz), 7.76 (d, 1H, J, 1.9 Hz), 8.04(d, 2H, J, 8.5 Hz).

Workup

  1. customwas de-gassed under vacuum)
  2. filtrationThe solution was filtered through wet celite
  3. washthe celite washed with EtOH
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-687e8664e7d640bbb5688ba951db292f
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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