HCID 59754787, compound → HCID 16719077, compound

HRID 751435Notes

Reaction equation

HRID 751435 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]3[CH:9]=[C:8]2/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:4][CH:3]=1>CCO.CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]3[CH:9]=[C:8]2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:23][CH:24]=1

Participants

5

Reactant 1

HCID 59754787HCID 59754787, compound

Product 1

HCID 16719077HCID 16719077, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-[1-(4-Chloro-benzyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-acrylic acid (Example 1; 95 mg, 0.277 mmol) in a mixture of EtOH (2 mL) and EtOAc (2 mL) was added Pd/C (˜20 mg) and maintained under an atmosphere of H2 for 12 hrs. The resulting slurry was filtered through celite eluting with EtOAc, and the solvent evaporated to afford the title acid as a colorless solid. LCMS (ESI) M+H 345.

Workup

  1. temperaturemaintained under an atmosphere of H2 for 12 hrs
  2. filtrationThe resulting slurry was filtered through celite
  3. washeluting with EtOAc
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-ee8a0bc2dcaa4f8c9a9cb0f6c73d858f
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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