Application of 934524-10-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 934524-10-4 as follows.
To a solution of 3-propylthiophene (1.3 g, 10 mmol) in anhydroud THF (25 rnL) cooled at -78 0C under argon atmosphere was added ra-BuLi (2.5 M in hexanes; 4.4 mL, 11 mmol). The mixture was stirred at the same temperature for 15 min and trimethyllborate added (2.2 mL, 20 mmol). The resulting mixture was stirred at at -78 0C for 15 min and then stirred at RT for 2 h. The reaction was quenched with IM HCl (3 mL) and concentrated. The residue was taken up in water (40 mL) and extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the crude product purified by silica gel column (CHCl3 to 10% CH3OH/CHCI3) to afford 4-propylthiophen-2-yl-2-boronic acid as an off-white solid (0.5 g, 29%). A mixture of 8 (0.28 g, 0.82 mmol), 4-propylthiophen-2-yl-2-boronic acid (0.17 g, 1.0 mmol), Pd(PPh3)4 (96 mg, 0.08 mmol) and Na2CO3 (0.32 g, 3 mmol) in anhydrous DMF (10 mL) was degassed with argon for 2 min and then heated at 120 0C in a sealed tube for 2 h. After cooling to room temperature, the solvent was removed by rotovap. The crude product was then purified by silica gel column with 1 : 1 hexanes/CHCl3 as an eluent to yield a yellow solid (90 mg, 25%).[0346] 1H NMR (500 MHz, CDCl3): delta 0.96 (t, J = 7.4 Hz, 3H), 1.60-1.75 (m, 2H), 2.42 (s, 3H), 2.63 (t, J = 1.6 Hz, 2H), 6.95 (d, J = 4.0 Hz, IH), 7.22 (s, IH), 7.74 (d, J = 4.2 Hz, IH), 7.79 (s, IH), 8.13 (d, J = 8.4 Hz, 2H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.
Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
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