Related Products of 10602-06-9,Some common heterocyclic compound, 10602-06-9, name is Methyl 3-ethynylbenzoate, molecular formula is C10H8O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 75: Synthesis of 3-[2-(l,3-thiazol-4-yl)ethynyl]benzoic acid: 3-[2-(l,3-thiazol-4-yl)ethynyl]benzoic acid. A mixture of 3-ethynyl-l-yl- benzoic acid methyl ester (40 mg, 0.25 mmol), 4-bromo-thiazole (82 mg, 0.5 mmol), palladium tetrakis-triphenylphosphine (29 mg, 0.025 mmol) and copper iodide (9.5 mg, 0.05 mmol), potassium carbonate (69 mg, 0.5 mmol) in 1,2- dimethoxyethane/water (1 mL/0.3 mL) was degassed with N2 for 5 minutes and then heated at 60 C for 4 hours. After cooling to ambient temperature, the crude mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated and purified by preparative thin layered chromatography eluting with ethyl acetate/hexane (30%) to give the ester intermediate. To this intermediate in tetrahydrofuran/methanol (1 mL/0.2 mL) was added sodium hydroxide solution (2 N in water, 0.2 mL, 0.4 mmol) and the solution was stirred at room temperature for 18 hours. 1 N hydrochloric acid aqueous solution was added dropwise until pH = 1 and the reaction mixture was purified through preparative HPLC to give 18 mg (22% for 2 steps) of the pure product as a white solid. FontWeight=”Bold” FontSize=”10″ H NMR (300MHz, DMSO) delta = 13.2 (br. s., 1H), 9.18 (d, J=2.1 Hz, 1H), 8.19 (d, J=1.8 Hz, 1H), 8.05 (t, J=1.5 Hz, 1H), 7.98 (td, J=1.4, 7.8 Hz, 1H), 7.81 (td, J=1.4, 7.8 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H). LCMS (ESI) mlz 230.0 (M+l)+. Example 77: Synthesis of 3-[2-(lH-indol-5-yl)ethynyl]benzoic acid: 3-[2-(lH-indol-5-yl)ethynyl]benzoic acid was prepared by the same procedure as example 75. NMR (300MHz, CDC13) delta = 9.30 (br. s., 1H), 8.23 (t, J=1.8 Hz, 1H), 7.98 (td, J=1.5, 7.9 Hz, 1H), 7.87 (d, J=0.9 Hz, 1H), 7.72 (td, J=1.3, 7.9 Hz, 1H), 7.47 – 7.23 (m, 4H), 6.59 – 6.50 (m, 1H). LCMS (ESI) mlz 262.0 (M+l)+.
The synthetic route of 10602-06-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE WISAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy, E.; SMITH, Garry, R.; REITZ, Allen, B.; LIEBERMAN, Paul, M.; WO2015/73864; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics