HCID 178422448, compound → HCID 178425384, compound

HRID 1890336Notes

Reaction equation

HRID 1890336 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N:9]2[C:13]3=[N:14][C:15]([OH:18])=[CH:16][CH:17]=[C:12]3[N:11]=[CH:10]2)=[C:4]([CH3:19])[CH:3]=1>CO.[OH-].[Pd+2].[OH-]>[Cl:8][C:7]1[CH:2]=[CH:3][C:4]([CH3:19])=[C:5]([N:9]2[C:13]3=[N:14][C:15]([OH:18])=[CH:16][CH:17]=[C:12]3[N:11]=[CH:10]2)[CH:6]=1

Participants

4

Reactant 1

HCID 178422448HCID 178422448, compound

Product 1

HCID 178425384HCID 178425384, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-bromo-5-chloro-2-methylphenyl)-3H-imidazo[4,5-b]pyridin-5-ol (320 mg, 0.95 mmol) in MeOH (8.0 mL) was added palladium hydroxide (20% on carbon, 65 mg). The mixture was placed in a Parr shaker under H2 (30 psi) for 12 h, filtered through Celite® and concentrated. The mixture was purified by preparative HPLC to give the title compound as a white solid. LCMS m/z=260.1, [M+H]+.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-5616b8b669f94c5ba42b21f5b166aaf8
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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