Application of 82231-58-1, These common heterocyclic compound, 82231-58-1, name is Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate, 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.
[00393] To a mixture of 58-8 (200.0 mg, 0.6 mmol, 1.00 eq), 58-3 (154.0 mg, 0.7 mmol, 1.20 eq) and Na2C03 (116.7 mg, 1.1 mmol, 2.00 eq) in dioxane (4.0 mL) and H20 (0.5 mL), was added Pd(dppf)Cl2 (40.3 mg, 55.1 umol, 0.10 eq). The mixture was degassed under vacuum and purged with N2 3 times. The resulting mixture was stirred at 100 C for 17 h. LCMS showed the reaction was complete. The mixture was concentrated under vacuum. The residue was purified by silica gel chromatography to afford the crude products. The crude products were purified by prep-HPLC (acidic HC1 condition) to provide Compound 58 and Compound 59. [00394] Compound 58: 2.31 mg, 4.4 umol, 0.8% yield, HC1. LCMS (ESI): RT = 0.852 min, mass calc. for C20Hi8F3N3O2 389.14, m/z found 390.0 [M+H]+. 1HNMR (400MHz, CHLOROF ORM-i ) 7.74 (s, 1H), 7.66 (s, 1H), 7.41 (dd, J= 1.5, 7.5 Hz, 1H), 7.38 – 7.31 (m, 2H), 7.29 – 7.24 (m, 1H), 7.20 (s, 1H), 7.15- 7.06 (m, 3H), 5.78 (s, 1H), 4.94 (s, 2H), 4.26 (q, J= 7.0 Hz, 2H), 1.30 (t, J= 7.2 Hz, 3H). [00395] Compound 59: 52.51 mg, 0.1 mmol, 24.0% yield, HC1. LCMS (ESI): RT = 0.783 min, mass calc. for Ci8Hi4F3N302 361.10, m/z found 361.9 [M+H]+. 1HNMR (400MHz, METHANOL-d4) 7.81 (s, 1H), 7.65 (s, 1H), 7.49 (d, J= 7.5 Hz, 1H), 7.34- 7.27 (m, 2H), 7.26 – 7.21 (m, 1H), 7.15- 7.10 (m, 1H), 7.09 – 7.06 (m, 2H), 6.97 (d, J= 7.8 Hz, 1H), 4.77 (s, 2H).
Statistics shows that Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate is playing an increasingly important role. we look forward to future research findings about 82231-58-1.