HCID 86707296, compound → HCID 86707295, compound

HRID 576088Notes

Reaction equation

HRID 576088 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][N:24]([C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=1)=[O:30])[CH2:23]2)(=[O:19])=[O:18])C1C=CC=CC=1>C(O)C.[Pd]>[C:38]([C:35]1[CH:34]=[CH:33][C:32]([NH:31][C:29]([N:24]2[CH2:23][C:22]3[C:26](=[CH:27][CH:28]=[C:20]([S:17](=[O:18])(=[O:19])[NH:16][C:10]4[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=4[OH:8])[CH:21]=3)[CH2:25]2)=[O:30])=[CH:37][CH:36]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

4

Reactant 1

HCID 86707296HCID 86707296, compound

Product 1

HCID 86707295HCID 86707295, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-{[2-(benzyloxy)-4-fluorophenyl]sulfamoyl}-N-(4-tert-butylphenyl)-1,3-dihydro-2H-isoindole-2-carboxamide (150 mg, 0.261 mmol) in ethanol (10 mL) was added 10% palladium activated carbon (150 mg) at room temperature, and the mixture was stirred overnight under a hydrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=19:1), powdered with hexane, and then collected by filtration to afford the title compound as a brownish red powder (98.4 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite (registered trademark)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=19:1)
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8de8a29a8d6d417e87853720dfc5a085
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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