Cesium carbonate → 7-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

HRID 1993390Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:28][C:29]1[CH:30]=[C:31]([N+:36]([O-:38])=[O:37])[CH:32]=[CH:33][C:34]=1F>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:34]3[CH:33]=[CH:32][C:31]([N+:36]([O-:38])=[O:37])=[CH:30][C:29]=3[F:28])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred suspension of 7-(benzyloxy)-6-methoxyquinolin-4-ol (4.0 g, 14.2 mmol) and Cs2CO3 (11.5 g, 35.5 mmol) in DMF (40 mL) at 40° C. under N2 was added 3,4-difluoronitrobenzene (1.6 mL, 14.2 mmol). The suspension stirred at 40° C. for 45 min. Solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (150 mL) and 1 N NaOH (50 mL). The organic layer was washed with water (50 mL) and brine (25 mL) and purified on silica gel yielding the title compound. Calc'd Mass for C23H17FN2O5, 420, MS (M+1) 421.

Workup

customSolvent was removed under reduced pressure
customthe residue was partitioned between CH2Cl2 (150 mL) and 1 N NaOH (50 mL)
washThe organic layer was washed with water (50 mL) and brine (25 mL)
custompurified on silica gel yielding the title compound

Sources & evidence

ORD record: ord-2465d2bd265f48399d75e49709e2e080
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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