HCID 57743064, compound → HCID 57743040, compound

HRID 1924237Notes

Reaction equation

HRID 1924237 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:23])[C:6]=1[CH2:7][N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=2[F:21])[CH2:10][C:9]1=[O:22]>CO.[Pd]>[CH3:23][N:5]1[C:6]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:2][CH:3]=[N:4]1

Participants

4

Reactant 1

HCID 57743064HCID 57743064, compound

Product 1

HCID 57743040HCID 57743040, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 250 ml pressure jar, under inert atmosphere, 1-[(4-bromo-1-methyl-1H-pyrazol-5-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 182 (0.41 g, 1 mmol) is dissolved in MeOH (50 ml). Pd on charcoal (82 mg, 20% w/w) is added and the mixture is hydrogenated under a pressure of 40 psi at room temperature for 3 h. The mixture is filtered on Celite and concentrated to dryness. The residue is purified by column chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 98/1.8/0.2 (v/v/v)) and recrystallized from diisopropylether to afford 0.18 g of 1-[(1-methyl-1H-pyrazol-5-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 183.

Workup

  1. filtrationThe mixture is filtered on Celite
  2. concentrationconcentrated to dryness
  3. customThe residue is purified by column chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 98/1.8/0.2 (v/v/v))
  4. customrecrystallized from diisopropylether

Sources & evidence

ORD record
ord-ee708f9028be464ebef2bb786d051dba
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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