Lithium Hydroxide → HCID 90318783, compound

Participants

Reaction Conditions

Reaction Steps

To methyl 5-(2-chloroquinoline-3-carboxamido)picolinate (52.26 mg, 0.15 mmol), 2-chloro-4-fluorophenol (21.98 mg, 0.15 mg), potassium carbonate (62.19 mg, 0.45 mmol) and 1-methylpyrrolidin-2-one (1 mL) were added and the reactions were stirred at 100° C. for 1 hour. 2M lithium hydroxide (75 μL, 0.45 mmol) and methanol (150 μL) were added and the reaction stirred at 50° C. for 2 hours. The reaction was filtered and (75 μL, 0.45 mmol) of 2M lithium hydroxide were added and stirring was continued for an additional 2 hours. The reaction was filtered and purified by reverse phase preparative chromatography utilizing a gradient of 10-99% acetonitrile in water containing HCl as a modifier to yield 5-(2-(2-chloro-4-fluorophenoxy)quinoline-3-carboxamido)picolinic acid hydrochloric acid (79) (4.2 mg, 6%). ESI-MS m/z calc. 437.06, found 338.4 (M+1)+)+; Retention time: 1.49 minutes (3 minutes run).

Provenance & Evidence