Cesium carbonate → 7-(2,4-difluorophenoxy)-1-(2,6-difluorophenyl)-2H-quinolizin-2-one

HRID 1454979Notes

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.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[OH:29].CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.C(OCC)(=O)C.Cl[Cu]>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[O:29][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

Conditions

Temperature: 120 °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-difluorophenol (0.06 ml, 0.6 mmole), 2,2,6,6-tetramethylheptane-3,5-dione (0.007 ml, 0.03 mmole), CuCl (15 mg, 0.15 mmole) and cesium carbonate (195 mg, 0.6 mmole) in NMP. The mixture was heated to 120° C. until the reaction completed. The mixture was diluted with ethyl acetate, washed with 1N HCl, 1N NaOH, brine, dried over MgSO4, and concentrated to yield crude material. The crude material was purified by silica gel chromatography (CH2Cl2/acetone) to yield the title compound.

Workup

washwashed with 1N HCl, 1N NaOH, brine
dry with materialdried over MgSO4
concentrationconcentrated
customto yield crude material
customThe crude material was purified by silica gel chromatography (CH2Cl2/acetone)

Sources & evidence

ORD record: ord-0e56735d6a7f4e929fb19d752382a4ed
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482345B2

Reaction notes

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