Quinoline → HCID 9815958, compound

HRID 1934354Notes

Reaction equation

HRID 1934354 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:5])[C:3]#[CH:4].N1C2C(=CC=CC=2)C=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:5][C:2]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:1])[CH:3]=[CH2:4]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 9794500HCID 9794500, compound

Product 1

HCID 9815958HCID 9815958, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

Five percent Pd/BaSO4 (100 mg) was added to a solution of N-(1,1-dimethyl-2-propynyl)-2,4-difluorobenzamide obtained in Example 36 (1.0 g, 4.5 mmol) and quinoline (100 mg) in methanol (20 ml), and stirred under a hydrogen atmosphere at room temperature for 1.5 hours. The catalyst was removed by filtration and the filtrate was concentrated under a reduced pressure. The residue was diluted with ethyl acetate and washed, with 1N hydrochloric acid (×3), saturated aqueous NaHCO3 and brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give the title compound (0.95 g; 94%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed, with 1N hydrochloric acid (×3), saturated aqueous NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-9d2d21feacf6489cb77da178d06eb8d7
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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