Methyl iodide → HCID 54581661, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-fluoro-1-(1H-indazol-5-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.092 g, 0.25 mmol) in anhydrous N,N-dimethylformamide (0.8 mL) was added methyl iodide (0.10 mL, 1.60 mmol). The solution was cooled to 0° C. and sodium hydride (0.011 g, 0.28 mmol) was added. After stirring for 10 minutes at that temperature the reaction was quenched with water and 2 ml of a saturated aqueous lithium hydroxide solution was added. After stirring for 30 min, the solution was acidified with 4 N HCl and the product was extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by reverse phase HPLC to provide the 5-fluoro-1-[(1-methyl-1H-indazol-5-yl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. The 5-fluoro-1-[(2-methyl-2H-indazol-5-yl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was isolated as the minor product. 5-Fluoro-1-[(1-methyl-1H-indazol-5-yl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 352 for M+H+. 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.96 (s, 1H), 7.66-7.60 (m, 1H), 7.54 (s, 1H), 7.44 (d, J=8.7 Hz, 1H), 7.37 (d, J=8.7 Hz, 1H), 7.22-7.15 (m, 2H), 5.59 (s, 2H), 4.08 (s, 3H).

Provenance & Evidence