HCID 68426898, compound → 4-Hydroxy-1,2-diphenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642275Notes

Reaction equation

HRID 642275 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14](Br)=[C:13]([C:16]3[CH:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]>C(O)C.CN(C=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 68426898HCID 68426898, compound

Product 1

HCID 684284944-Hydroxy-1,2-diphenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 27.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-bromo-2-(4-chloro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (200 mg, 0.42 mmol)(from Example 36(d)) in ethanol (12 mL) and DMF (3 mL) was added Pd/C (10% wet, containing 50% water)(120 mg) was stirred under hydrogen atmosphere (balloon pressure) for 30 h. Reaction mixture was filtered through a pad of celite and rinsed with EtOAc. Filtrate was concentrated and purified by silica gel chromatography (eluting with 25%-50% EtOAc/hexanes) to give the title compound 42 mg. MS-(+)-ion: M+1=359.04.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through a pad of celite
  3. washrinsed with EtOAc
  4. concentrationFiltrate was concentrated
  5. custompurified by silica gel chromatography (eluting with 25%-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-75512bdd95a84b4d91a64d7f8f63abf1
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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