Hydrochloric Acid → Indolin-5-yl 4-isopropylphenylcarbamate

HRID 2360136Notes

Reaction equation

HRID 2360136 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:29])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18](CC2C=CC=CC=2)[CH2:17][CH2:16]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>[Pd].C(O)(C)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:29])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 468661431-Benzylindolin-5-yl 4-isopropylphenylcarbamate

Product 1

HCID 86659865Indolin-5-yl 4-isopropylphenylcarbamateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 1-benzylindolin-5-yl 4-isopropylphenylcarbamate (300 mg, 0.776 mmol) in a 2:1 solution (3.0 mL) of isopropylalcohol and 6 M HCl was added palladium 10% on carbon (30 mg) under nitrogen. After the vessel was purged with hydrogen, the reaction mixture was stirred under 1 atm of hydrogen at room temperature overnight. After the vessel was purged with nitrogen, the reaction mixture was filtered to remove palladium 10% on carbon. The filtrate was concentrated in vacuo. After the residue was diluted with ethyl acetate, the solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, 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 (220 mg, 96%).

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 10% on carbon
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionAfter the residue was diluted with ethyl acetate
  7. washthe solution was washed with saturated NaHCO3 aqueous solution, brine
  8. dry with materialdried over MgSO4
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated in vacuo
  11. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15 to 40/60)

Sources & evidence

ORD record
ord-fd798d5e74d34ef98d8b7aeaf2b57b7f
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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