4-[2-Carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-[2-carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 18163Notes

Reaction equation

HRID 18163 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([C:31](=[O:33])[NH2:32])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([C:31](=[O:33])[NH2:32])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 685845934-[2-Carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 685859844-[2-carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl esterYield 48.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[2-Carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (156 mg, 0.35 mmol) in EtOH (20 ml) was added to a Parr vessel containing catalytic amount of 5% Pd on carbon. The vessel was purged with H2 at the pressure of 50 psi (3.45 bar). After shaking overnight, the reaction mixture was filtered through Celite and concentrated. The brown residue was purified by flash chromatography to give 4-[2-carbamoyl-1-(3-fluoro-benzyl)-1H-indol-4-yl]-piperidine-1-carboxylic acid tert-butyl ester as yellow solid (76 mg, 48%).

Workup

  1. customThe vessel was purged with H2 at the pressure of 50 psi (3.45 bar)
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customThe brown residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fe8e3ab991134d0ebb273f0706bbddff
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

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