Category: 82231-58-1

Electric Literature 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.

Step 3: Ethyl [4-(2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidin-5-yl)-1H-pyrazol-1-yl]acetateInto a 50-mL round-bottom flask equipped with a magnetic stirbar and reflux condenser was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidine (311 mg, 1.35 mmol), ethyl (4-bromo-1H-pyrazol-1-yl)acetate (400 mg, 0.89 mmol), PdCl2(dppf) (36 mg, 0.05 mmol), 2 M aqueous sodium carbonate solution (0.89 mL, 1.8 mmol) and DMF (4 mL). The resulting suspension was degassed under nitrogen for 20 min and then heated in the microwave to 120 C. for 20 min. The mixture was poured into a 125-mL separatory funnel containing a saturated aqueous KH2PO4 solution (50 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification by column chromatography through silica gel, eluting with 30% EtOAc in hexanes to 70% EtOAc in hexanes as a gradient gave the title compound as a white solid. MS (ESI, Q+) m/z 476 (M+1).

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.

Reference:
Patent; Leblanc, Yves; Powell, David; Ramtohul, Yeeman K.; Leger, Serge; US2008/182838; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82231-58-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 82231-58-1, name is Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4,4,5,5-tetramethyl- 2-(4,4,5,5-tetramethyl (1,3.2 – dioxaborolan-2-yl)) -1,3,2-dioxaborolane (436mg, 1.72mmol) in DMF (1OmL) at O0C were added KOAc (420mg, 4.29mmol) and Pd(dppf)Cl2.CH2Cl2 (35mg, 0.043mmol). The reaction mixture was heated to 8O0C at which point a solution of 27b (333mg, 1.43mmol) in DMF (1OmL) was added drop-wise. The resulting mixture was stirred at 8O0C overnight and evaporated to dryness. The residue was chromatographed on silica gel (ethyl acetate/petrol=l : 10) to provide 27c (76mg, 19%).

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, Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference 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.

Step 3: Ethyl [4-(2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidin-5-yl)-1H-pyrazol-1-yl]acetateInto a 50-mL round-bottom flask equipped with a magnetic stirbar and reflux condenser was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidine (311 mg, 1.35 mmol), ethyl (4-bromo-1H-pyrazol-1-yl)acetate (400 mg, 0.89 mmol), PdCl2(dppf) (36 mg, 0.05 mmol), 2 M aqueous sodium carbonate solution (0.89 mL, 1.8 mmol) and DMF (4 mL). The resulting suspension was degassed under nitrogen for 20 min and then heated in the microwave to 120 C. for 20 min. The mixture was poured into a 125-mL separatory funnel containing a saturated aqueous KH2PO4 solution (50 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification by column chromatography through silica gel, eluting with 30% EtOAc in hexanes to 70% EtOAc in hexanes as a gradient gave the title compound as a white solid. MS (ESI, Q+) m/z 476 (M+1).

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.

Reference:
Patent; Leblanc, Yves; Powell, David; Ramtohul, Yeeman K.; Leger, Serge; US2008/182838; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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.