15366-34-4, A common compound: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, belongs to pyrazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
Methyl 1H-pyrazole-3-carboxylate (0.500 g, 3.96 mmol), was dissolved in DCE (25 mL), then cyclopropylboronic acid (0.681 g, 7.93 mmol) and sodium carbonate(0.840 g, 7.93 mmol) were added. The reaction mixture was heated to 70 C, and then a mixture of 2,2?-bipyridine (0.6 19 g, 3.96 mmol) and copper(II) acetate (0.720 g, 3.96 mmol) were added in one batch. The reaction mixture was stirred at 70 C under oxygen atmosphere (1 atm) for 2 d. Saturated aq. NaHCO3 solution was added to the reaction mixture, and it was extracted with EtOAc (3x). The combined organic phase was concentrated. The residue was purified by flash chromatography (solid loading on CELITE, 0-65% EtOAc/Hex) affording two products.Intermediate 15A (0.119 g, 18% yield) as a colorless syrup eluted at 2O% EtOAc. MS(ESI) m/z: 167.0 (M+H) ?H NMR: (400 MHz, DMSO-d6) oe ppm 7.40 (d,J=2.0 Hz, 1H), 6.82 (d, J=2.0 Hz, 1H), 4.31 -4.24 (m, 1H), 2.11 (s, 3H), 1.29- 1.22 (m,2H), 1.10- 1.00 (m, 2H).Intermediate 16A (0.37 1 g, 56% yield) as a colorless syrup eluted at 45% EtOAc. MS(ESI) m/z: 167.0 (M+H) ?H NMR: (400 MHz, DMSO-d6) oe ppm 77.46 (d, J=2.4 Hz, 1H), 6.78 (d, J=2.2 Hz, 1H), 3.92 (s, 3H), 3.67 (tt, J=7.4, 3.9 Hz, 1H), 1.23 -1.15 (m, 2H), 1.09- 1.01 (m, 2H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.