Dimethylformamide → 2-t-Butoxycarbonyl-9-(2-oxo-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 2301091Notes

Reaction equation

HRID 2301091 reaction equation
CN(C=[O:5])C.[C:6]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:26][CH:27]=[CH2:28])[C:15]=2[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>[Pd](Cl)Cl.C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:26][C:27](=[O:5])[CH3:28])[C:15]=2[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 108599292-t-Butoxycarbonyl-9-allyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Product 1

HCID 183773662-t-Butoxycarbonyl-9-(2-oxo-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleYield 59%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium chloride (100 mg) and cupric chloride dihydrate (50 mg) were added to DMF solution (30 ml) of 2-t-butoxycarbonyl-9-allyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1.90 g, 6.1 mmol) and stirred at room temperature for 18 hours. The reaction solution was mixed with ethyl acetate, washed with water and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure, the thus obtained residue was mixed with diisopropyl ether (20 ml) and the thus precipitated crystals were collected by filtration to obtain 1.17 g of the title compound (59% in yield).

Workup

  1. washwashed with water
  2. dry with materialdried with anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation under a reduced pressure
  4. additionthe thus obtained residue was mixed with diisopropyl ether (20 ml)
  5. filtrationthe thus precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ad67b9fa118c4d9e9ad44f503c34637d
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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