Category: 139308-52-4

Related Products of 139308-52-4, These common heterocyclic compound, 139308-52-4, name is Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, 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.

[1302] to a solution of ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate (500 mg, 2.15 mmol) and NCS (574 mg, 4.30 mmol) was stirred. The mixture was stirred at 160 C for 3h under N2. The reaction mixture was added by addition of cc (20 ml), and then diluted with NaHCO3 (30 ml). The mixture was extracted with DCM (20 ml x 3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by preparatory- tlc (SiO2, pe:ea = 5: 1). Compound 274a (180 mg, yield: 31.30%) was obtained as a yellow oil. 1H NMR (400mhz, CDCl3) delta 4.34 (q, = 7.1 hz, 2h), 3.85 (s, 3h), 1.46 – 1.24 (m, 3h). MS (ESI) m/z (M+H)+266.9.

The synthetic route of 139308-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 139308-52-4 as follows. Safety of Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate

[1042] a mixture of compound 163c (2 g, 8.58 mmol), meb(oh)2 (2.05 g, 34.3 mmol), pd(pph3)4 (793 mg, 687 umol), K2CO3 (2.37 g, 17.2 mmol) in dioxane (50 ml) and H2O (10 ml) was degassed and purged with n2 for 3 times, and then the mixture was stirred at 120 C for 12 hour under N2 atmosphere. The reaction mixture was extracted with ethyl acetate 50 ml (50 ml x 2). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate = 100: 1 to 80: 1). Compound 408a (1.4 g, yield: 97.0%) was obtained as a yellow solid. 1H NMR (400mhz, CDCl3) delta 7.87 – 7.73 (m, 1h), 4.27 (q, j = 7.1 hz, 2h), 3.91 -3.75 (m, 3h), 2.51 – 2.40 (m, 3h), 1.33 (t, j = 7.1 hz, 3h).

According to the analysis of related databases, 139308-52-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 139308-52-4, The chemical industry reduces the impact on the environment during synthesis 139308-52-4, name is Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

(4-(((Trans)-4-morpholinocyclohexyl)amino)quinazolin-6-yl)boronic acid (30 mg, 0.084mmol) was dissolved in EtOH (1 mL) and added to a vial containing ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate (29.0 mg, 0.126 mmol) and Si-DPP-Pd (64.8 mg, 0.0 17mmol). Potassium carbonate (1M in water, 0.084 ml, 0.168 mmol) was added, the vial wassealed and the resulting mixture was then heated to 125 C for 10 minutes under microwave irradiation. The mixture was filtered and purified by mass triggered reverse phase HPLC (ACN/water with 0.1% TFA modifier) to afford the title product as a TFA salt. MS: 465 (M+1). ?H NMR (DMSO-d6, 600 MHz) oe 9.79 (s, 1H), 8.89 (s, 1H), 8.75 (s, 1H), 8.48 (s,1H), 8.25 (d, J = 8.69 Hz, 1H), 7.81 (d, J = 8.67 Hz, 1H), 4.39 (br s, 1H), 4.14 (q, J = 7.10 Hz, 2H), 4.02-4.00 (m, 2H), 3.95 (s, 3H), 3.71-3.69 (m, 2H), 3.44-3.39 (br s, 1H), 2.52-2.50 (m, 4H), 2.20-2.18 (m, 2H), 2.10-2.08 (m, 2H), 1.64-1.58 (m, 4H), 1.16 (t,J= 7.10 Hz, 3H).

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 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; ANDRESEN, Brian, M.; BRUBAKER, Jason, D.; CHILDERS, Matthew, L.; DONOFRIO, Anthony; FISCHMANN, Thierry; GIBEAU, Craig, R.; KATTAR, Solomon, D.; LESBURG, Charles, A.; LIM, Jongwon; MACLEAN, John, K. F.; MANSOOR, Umar, F.; NORTHRUP, Alan, B.; SANDERS, John, M.; SMITH, Graham, F.; TORRES, Luis; (91 pag.)WO2016/53771; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 139308-52-4,Some common heterocyclic compound, 139308-52-4, name is Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H9BrN2O2, 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.

The reaction mixture of ethyl 3-bromo-1-methyl-pyrazole-4-carboxylate (200 mg, 0.86 mmol), 4-methoxypiperidine (197.67 mg, 1.72 mmol), Cs2CO3 (838.79 mg, 2.57 mmol) and XtanTphos Pd G3 (162.76 mg, 0.17 mmol) in dimethylacetamide (5 mL) was heated at 120 C. overnight. The reaction mixture was cooled down, washed with water, extracted with EtOAc, dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (0-100% EtOAc/hexane) to give the product (14 mg).

The synthetic route of 139308-52-4 has been constantly updated, and we look forward to future research findings.

Reference of 139308-52-4,Some common heterocyclic compound, 139308-52-4, name is Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H9BrN2O2, 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.

[0941] to a solution of compound 163c (2.6 g, 11.16 mmol) in MeOH (10 ml) and H2O (10 ml) was added LiOH.H2O (2.34 g, 55.80 mmol). The mixture was stirred at 25 C for 12h. The reaction mixture was concentrated and added 20 ml of water and the mixture was extracted with mtbe (20 ml x 2), the aqueous layer was acidified by in HCl to ph ~ 2-3 at 0 C, and extracted with EtOAc (30 ml x 2), the organic phase was dried over Na2SO4 and concentrated to give a residue. Compound 163f (2.2 g, yield: 96.16%) was obtained as a gray solid, which was used for next step directly. 1H NMR (400mhz, DMSO-d6) delta 12.55 (br s, 1h), 8.24 (s, 1h), 3.81 (s, 3h).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, its application will become more common.