7-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one → 7-(2,4-difluorobenzyl)-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

HRID 1454980Notes

Reaction equation

HRID 1454980 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:4]([CH:5]=[CH:6][C:7](=[O:20])[C:8]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1.[Br-].[F:22][C:23]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:24]=1[CH2:25][Zn+]>C1COCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:23]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:24]=1[CH2:25][C:2]1[CH:11]=[CH:10][C:9]2[N:4]([CH:5]=[CH:6][C:7](=[O:20])[C:8]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1

Participants

6

Reactant 2

HCID 575312307-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-oneHCID 178505768HCID 178505768, compound

Product 1

HCID 167496337-(2,4-difluorobenzyl)-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 7-bromo-1-(2,6-difluorophenyl)-2H-quinolizin-2-one (100 mg, 0.3 mmole) was added 2,4-difluorobenzylzincbromide (0.5 N in THF, 1.2 ml), and tetrakis (15 mg) in THF. The mixture was heated to 90° C. until reaction complete. The mixture was diluted with ethyl acetate, washed with 1N HCl, brine and dried over MgSO4. Upon concentration, the mixture was purified by gel chromatography (100% ethyl acetate) to yield the title compound.

Workup

  1. washwashed with 1N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationUpon concentration
  4. customthe mixture was purified by gel chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-ac211283edc340bf8f0682882680f728
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

Loading…