HCID 66670153, compound → HCID 66670292, compound

HRID 1514644Notes

Reaction equation

HRID 1514644 reaction equation
[CH3:1][N:2]([CH3:31])[CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:9]([CH3:20])=[C:8]([C:21]([O:23]CC2C=CC=CC=2)=[O:22])[CH:7]=1>C(O)C.O1CCCC1.[Pd]>[CH3:31][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C:9]([CH3:20])=[C:8]([C:21]([OH:23])=[O:22])[CH:7]=1

Participants

5

Reactant 1

HCID 66670153HCID 66670153, compound

Product 1

HCID 66670292HCID 66670292, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 501 mg portion of benzyl 5-[3-(dimethylamino)propyl]-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate was dissolved in a mixed solvent of 1 ml ethanol and 5 ml tetrahydrofuran, and 119 mg of 10% palladium-activated carbon was added, followed by stirring at room temperature for 15 hours under an atmosphere of hydrogen. The reaction liquid was filtered through celite, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (methanol:chloroform=10:90-15:85-20:80), to obtain 342 mg of 5-[3-(dimethylamino)propyl]-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylic acid as a colorless solid.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. filtrationwas filtered through celite
  4. concentrationthe filtrate was concentrated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol:chloroform=10:90-15:85-20:80)

Sources & evidence

ORD record
ord-dd15e77b6ae94a6c98dfae195ad98eac
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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