HCID 86659872, compound → HCID 86659873, compound

HRID 2360147Notes

Reaction equation

HRID 2360147 reaction equation
[C:1]1([NH:7][C:8](=[O:26])[O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](CC2C=CC=CC=2)[CH2:14][CH2:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C)C.[OH-].[Pd+2].[OH-]>[C:1]1([NH:7][C:8](=[O:26])[O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH2:14][CH2:13]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86659872HCID 86659872, compound

Product 1

HCID 86659873HCID 86659873, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 1-benzylindolin-5-yl phenylcarbamate (30 mg, 87 μmol) in 3.0 mL of isopropylalcohol was added palladium hydroxide 10% on carbon (60 mg) under nitrogen. After the vessel was purged with hydrogen, the reaction mixture was stirred under 1 atm of hydrogen at room temperature for 3 h. After the vessel was purged with nitrogen, the reaction mixture was filtered to remove palladium hydroxide 10% on carbon. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15 to 40/60) to obtain the title compound as a white solid (11.5 mg, 52%).

Workup

  1. customAfter the vessel was purged with hydrogen
  2. customAfter the vessel was purged with nitrogen
  3. filtrationthe reaction mixture was filtered
  4. customto remove palladium hydroxide 10% on carbon
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15 to 40/60)

Sources & evidence

ORD record
ord-e4461a9d5b484dc490c1c8c1a8cd3432
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

Loading…