1-(2,6-difluorophenyl)-7-[(2,4-difluorophenyl)ethynyl]-2H-quinolizin-2-one → 1-(2,6-difluorophenyl)-7-[2-(2,4-difluorophenyl)ethyl]-2H-quinolizin-2-one

HRID 1454983Notes

Reaction equation

HRID 1454983 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10](=[O:29])[CH:11]=[CH:12][N:13]2[C:18]=1[CH:17]=[CH:16][C:15]([C:19]#[C:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])=[CH:14]2>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10](=[O:29])[CH:11]=[CH:12][N:13]2[C:18]=1[CH:17]=[CH:16][C:15]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])=[CH:14]2

Participants

4

Reactant 1

HCID 167496341-(2,6-difluorophenyl)-7-[(2,4-difluorophenyl)ethynyl]-2H-quinolizin-2-one

Product 1

HCID 167496501-(2,6-difluorophenyl)-7-[2-(2,4-difluorophenyl)ethyl]-2H-quinolizin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(2,6-difluorophenyl)-7-[(2,4-difluorophenyl)ethynyl]-2H-quinolizin-2-one in methanol was added a catalytic amount of Pd/C under hydrogen atmosphere (1 atm) for 1 hour. The mixture was filtered through celite and the filtrate was concentrated. The crude material was purified by silica gel (100% ethyl acetate) to give the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude material was purified by silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-cd99f1b24daa41e6a480e6b76662cb7b
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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