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With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 110℃; for 20h;
STEP 2. Methyl 5-fluoro-2-methvlnicotinate; A mixture of <strong>[847729-27-5]methyl 2-chloro-5-fluoronicotinate</strong> (step 1, 1.5 g, 7.91 mmol), tetrakis (triphenylphoshine)palladium (914 mg, 0.79 mmol), methyboronic acid (521 mg, 8.70 mmol) and potassium carbonate (3.28 g, 23.7 mmol) in 1,4-dioxane (20 ml) was heated at 110 C for 20 h under nitrogen atmosphere. The reaction mixture was filtered through a pad of celite (Celite(trademark) (diatomaceous earth) ) and the filtrate was concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (20/1 to 4/1) to afford 936 mg (64%) of the title compound: ¹H-NMR (CDCl3) No. 8.49 (1 H, d, J = 3.0 Hz), 7.93 (1 H, dd, J = 3.0, 8.7 Hz), 3.94 (3H, s), 2.81 (3H, s).
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;
21.3
STEP 3. Methvl 5-fluoro-2-methylnicotinate 1-oxide; To a cooled (0 °C) solution of methyl 5-fluoro-2-methyinicotinate (step 2,936 mg, 5.53 mmol) in dichloromethane (100 ml) was added 3-chlorobenzenecarboperoxoic acid (2.38 g, 13.8 mmol) and the reaction suspension was stirred overnight at room temperature. The reaction was quenched by the addition of sat. sodium thiosulfate solution and sat. sodium bicarbonate solution was added. The whole mixture was extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated to afford 1.12 g (quant. ) of title compound: ¹H-NMR (CDCI3) No. 8.40-8.03 (1H, m), 7.52 (1 H, dd, J = 2.3, 7.7 Hz), 3.96 (3H, s), 2.73 (3H, s).
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