HCID 16065181, compound → 6-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-2-oxo-2H-quinolizine-7-carboxylic Acid

HRID 1360709Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[C:15]([CH:16]=[CH:17][C:18]=1[CH2:19][OH:20])=[C:14]([C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[F:28])[C:13](=[O:29])[CH:12]=[CH:11]2.CC(C)=[O:32].OS(O)(=O)=O.O=[Cr](=O)=O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[C:15]([CH:16]=[CH:17][C:18]=1[C:19]([OH:32])=[O:20])=[C:14]([C:21]1[C:22]([F:28])=[CH:23][CH:24]=[CH:25][C:26]=1[F:27])[C:13](=[O:29])[CH:12]=[CH:11]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-7-(hydroxymethyl)-2H-quinolizin-2-one (Example 50, 100 mg) was added Jones reagent (0.5 mL, 4 N in sulfuric acid; prepared using procedure similar to that disclosed in Bowers, Halsall, Jones, and Lemin, J. Chem. Soc., (1953), 2548-2560) at 0° C. The mixture was stirred for a couple of hours at 0° C. until reaction complete and then quenched with isopropanol (1 mL). After stirring for 10 min (green solution), the mixture was filtered through celite and concentrated. The residue was diluted with ethyl acetate and washed with water, brine, dried over MgSO4 and concentrated to give title compound (87 mg).

Workup

customprepared
customat 0° C
customquenched with isopropanol (1 mL)
stirringAfter stirring for 10 min (green solution)
filtrationthe mixture was filtered through celite
concentrationconcentrated
additionThe residue was diluted with ethyl acetate
washwashed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-b821436a014b44959525e77dbe45ff94
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879875B2

Reaction notes

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