Electric Literature of 214614-81-0, These common heterocyclic compound, 214614-81-0, name is 4-Bromo-1-(2-hydroxyethyl)pyrazole, its 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.
To a mixture of compound 17 (600 mg, 0.242 mmol) and compound 16 (600 mg, 0.926 mmol) was added 2-(4-bromo-1H-pyrazol-1-yl)ethan-1-ol 18 (CAS Reg. No. 214614-81-0, 336 mg, 1.757 mmol) and K2CO3 (607 mg, 4.39 mmol) in dioxane (8 mL) and water (2.000 mL). Nitrogen gas was bubbled through the reaction mixture for 2 min. Then PdCl2(dppf)-CH2Cl2 adduct (154 mg, 0.188 mmol) was added. Nitrogen was bubbled into it for another 1 min. The reaction vessel was sealed and its contents were stirred at 80 C. for 5 h. The reaction mixture was cooled, diluted with ethyl acetate, and filtered. The filtrate was dried over Na2SO4 and concentrated. The crude product was purified by ISCO silica column (40 g), eluted with 20% MeOH in DCM, DCM gradient 0-40%. The desired fractions were concentrated to yield compound 19 (247 mg, 0.565 mmol, 45.0% yield). LCMS ESI: calculated for C23H27N7O3=438.2 (M+H+), found 438.1 (M+H+). 1H NMR (400 MHz, METHANOL-d4) delta 8.00 (s, 1H), 7.84 (s, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H), 5.13 (s, 2H), 4.34 (t, J=6.6 Hz, 2H), 4.26 (s, 2H), 4.14 (s, 3H), 3.92 (t, J=5.4 Hz, 2H), 1.84-1.65 (m, 2H), 1.59-1.37 (m, 2H), 1.00 (t, J=7.5 Hz, 3H).
Statistics shows that 4-Bromo-1-(2-hydroxyethyl)pyrazole is playing an increasingly important role. we look forward to future research findings about 214614-81-0.