Ethyl acetate hexane → HCID 23086738, compound

Participants

Reaction Conditions

Reaction Steps

5-Oxo-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnoline (200 mg, 0.65 mmol) obtained in Example 66 was dissolved in tetrahydrofuran (1 mL) and cooled to −20° C., followed by adding a tetrahydrofuran solution (0.26 mL, 0.78 mmol) of 3N methylmagnesium chloride to the reaction liquid and reacting for 3 hours while elevating temperature. To the reaction liquid was added distilled water (1 mL) to quench, followed by adding ethyl acetate (5 mL) and a 1N aqueous solution of sodium hydrogen sulfate (5 mL) for extraction, washing an organic layer with a saturated saline solution (3 ml), drying with sodium sulfate anhydride and purification of residue obtained by concentration using silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/1) to obtain an objective compound (74.1 mg, 35%) as pale yellow crystal.

Provenance & Evidence