Ammonium formate → HCID 68428987, compound

HRID 642272Notes

Reaction equation

HRID 642272 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:33])=[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]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:33])=[C:8]2[CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68428645HCID 68428645, compound

Product 1

HCID 68428987HCID 68428987, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 1-benzo[1,3]dioxol-5-ylmethyl-3-bromo-2-(4-chloro-phenyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (200 mg, 0.38 mmol)(from Example 35(e)) in EtOAc (4 mL) was added palladium/char coal (Pd/C)(10% wet, containing 50% water) (95 mg) and ammonium formate (HCO2NH4)(495 mg, 7.86 mmol). The mixture was refluxed for 2 h. After cooled, it was diluted with EtOAc and then filtered through a pad of celite. Filtrate was concentrated and the residue was purified by silica gel chromatography (eluting with 30%-60% EtOAc/hexanes) to give the title compound 125 mg. MS-(+)-ion: M+1=417.13.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperatureAfter cooled
  3. filtrationfiltered through a pad of celite
  4. concentrationFiltrate was concentrated
  5. customthe residue was purified by silica gel chromatography (eluting with 30%-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b29e9c3132b4488ab3d3272cdc78013d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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