Water → Methyl 8-bromo-6-fluoro-4-methoxyquinoline-2-carboxylate

HRID 1795342Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[CH:14]=1)=[CH:11][C:10]([F:16])=[CH:9][C:8]=2[Br:17])=[O:4].[C:18]([O-])([O-])=O.[K+].[K+].CI.O>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH3:18])[C:12]2[C:7](=[C:8]([Br:17])[CH:9]=[C:10]([F:16])[CH:11]=2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Alternatively, into a 100 mL 3 neck round bottom flask equipped with a reflux condenser, nitrogen inlet and magnetic stirrer is placed 350 mg (1.17 mmol, 1.0 equiv.) of 8-Bromo-6-fluoro4-oxo-1,4-dihydro-quinoline-2-carboxylic acid methyl ester and 242 mg (1.75 mmol, 1.5 equiv.) of K2CO3. This material is suspended in 20 mL of DMSO then heated to 70° C. for 1 hr. The anion formation of the anion is apparent when the mixture becomes cloudy. The mixture is allowed to cool to 35° C. then 331 mg, 145 μL (2.33 mmol, 2.0 equiv.) of methyl iodide are added and stirring is continued for 2 hr. At the end of this time it is determined if the reaction is complete by LC/MS. Upon completion the mixture is poured into 200 mL of water and the solids which form are collected by filtration and washed with water to give 340 mg (93%) of the O-methylated product after drying.

Workup

temperatureto cool to 35° C.
filtrationthe solids which form are collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-b8be0ab167dc45eb9647d5cf69817375
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026314B2

Reaction notes

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