Ammonium formate → HCID 68525452, compound

HRID 884125Notes

Reaction equation

HRID 884125 reaction equation
Br[C:2]1[C:3]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=2)=[N:4][CH:5]=[C:6]([S:8](=[O:21])(=[O:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:7]=1.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([NH:9][S:8]([C:6]2[CH:7]=[CH:2][C:3]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=3)=[N:4][CH:5]=2)(=[O:21])=[O:20])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59140820HCID 59140820, compound

Product 1

HCID 68525452HCID 68525452, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(4-(3-bromo-5-(N-(4-(trifluoromethyl)phenyl)sulfamoyl)pyridin-2-yloxy)phenyl)propionate (0.41 g, 0.7 mmol) in ethanol (10 mL) were added 10% palladium-carbon (0.041 g) and ammonium formate (0.226 g, 3.6 mmol), and the resulting solution was heated to reflux for 2 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was then purified by silica gel chromatography (n-hexane:ethyl acetate=4:1), to thereby yield 0.28 g of the title compound.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 2 hours
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was then purified by silica gel chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1c244e2b47a645449b08ad2cbc40eeea
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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