Category: 13808-64-5

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-3-methylpyrazole

4-Bromo-1-isopropyl-3-methyl-1H-pyrazole (B2.1) (0353) A mixture of 4-bromo-3-methyl-1H-pyrazole (2 g, 12.5 mmol), 2-iodopropane (6.37 g, 37.5 mmol), Cs2CO3 (6.25 g, 50 mmol) and acetonitrile (30 mL) was stirred at 90 C. for 12 h. The reaction mixture was filtered with MeOH (15 ml) and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (UV214, PE_DMC=100:1 to 50:50) to afford the title compound (700 mg, 56%) as a clear oil. LC-MS: [M+H]+=203.1.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; CHAN, Ho Man; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (134 pag.)US2016/176882; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 13808-64-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13808-64-5, name is 4-Bromo-3-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATIVE EXAMPLE 15; Step A; N-methyl-4-bromopyrazole-3-carboxylic acid was prepared according to known methods, see: Yu. A. M.; Andreeva, M. A.; Perevalov, V. P.; Stepanov, V. I. ; Dubrovskaya, V. A.; and Seraya, V. l. in Zh. Obs. Khim, (Journal of General Chemistry of the USSR) 1982,52, 2592 (and the references cited therein) the disclosure of whichis incorporated hereinby reference thereto.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methylpyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/66147; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H5BrN2

NaH (60% in mineral oil, 410 mg, 10.2 mmol) is added portionwise to a stirred solution of 4- bromo-3-methylpyrazole (1.69 g, 10.2 mmol) in DMF (20 ml). The resulting mixture is stirred for 1 h at 00C and 4-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (as obtained in preparation 61 , 2.839 g, 10.16 mmol) is added. The resulting pale suspension is heated at 950C for 1h. The reaction is quenched with water and extracted with EtOAc several times. The combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography on a 120 g silica gel column on a Combiflash Companion (Isco Inc.) apparatus ( gradient hexanes: TBDME from 1 :0 => 1 :1) to afford the two regioisomers identified by preparation 92 and preparation 93.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/148867; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 13808-64-5, A common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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.

Compound 11 is prepared from compound 10 by reacting (1 eq), Boc2O (1.5 eq), Na2CO3 (2 eq) in DCM at RT for 16 h. After work up and the NMR showed characteristic peaks and was used as such for the next step. In subsequent step compound II (1 eq), and 12 (1.1 eq) in presence of PdCl2(dppf) (0.05 eq), KOAc (3 eq), DMSO was heated to 90 C., 16 h. After column purification LCMS showed 50% of desired mass of compound 11. Key intermediate 14 was prepared was prepared by reacting (1 eq), BH3-DMS (3 eq), THF, RT, 16 h. After work up LCMS showed 96% purity of the compound 14.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BETA CAT PHARMACEUTICALS, LLC; Vankayalapati, Hariprasad M.; Horrigan, Stephen; US2013/123281; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 13808-64-5, A common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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.

A solution of potassium tert-butoxide (IM in THF, 18ml) was added to a solution of 4-bromo- 3-methylpyrazole (2.9Ig) in THF (20ml). The mixture was stirred at RT for 20min then dimethylsulfamoyl chloride (1.94ml) was added and stirred overnight. The solvent was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with 20% ethyl acetate/isohexane.1 H NMR DMSO-d6: delta 8.47 (IH, s), 2.85 (6H, s), 2.23 (3H, s)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/37982; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 4-Bromo-3-methylpyrazole

A mixture of 4-bro mo-3- methyl-i H-pyrazole (2 g, 12.5 mmol), 2-iodopropane (6.37 g, 37.5 mmol), C52CO3 (6.25 g, 50 mmol) and acetonitrile (30 mL) was stirred at 90 C for 12 h. The reaction mixture was filtered with MeOH (15 ml) and the filtrate was concentrated.The residue waspurified by flash chromatography on silica gel (UV214, PE:DMC = 100:1 to 50:50) to afford the title compound (700 mg, 56%) as a clear oil. LC-MS: [M+H] = 203.1.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H5BrN2

Step A: N-Boc-4-bromo-3-methyl-pyrazole. To 4-bromo-3-methyl-pyrazole (3.50 g, 21.7 mmol) was added CH2Cl2 (30 mL), di-tert-butyl dicarbonate (5.22 g, 23.9 mmol) and aq Na2CO3 (1 M, 43.5 mL). The reaction was stirred for 2.5 h and the aq portion was then separated. The CH2Cl2 portion was then washed with 5% citric acid followed by brine/saturated aq NaHCO3 (1:1). The solution was dried (Na2SO4), filtered and concentrated to afford the product.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Clements, Matthew J.; Debenham, John S.; Hale, Jeffrey J.; Madsen-Duggan, Christina B.; Walsh, Thomas F.; Peresypkin, Andrey V.; Helmy, Roy; US2008/269279; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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. Computed Properties of C4H5BrN2

10330] To a suspension of NaH 60% in oil (0.3 g; 7.45 mmol) in tetrahydrofuran (150 mE) there is added, at 100 C., 4-bromo-3-methyl-1H-pyrazole dissolved in 15 mE of tetrahydrofuran dropwise, over 15 minutes. Afier stirring for 40 minutes at ambient temperature, iodomethane (0.45 mE; 7.45 mmol) is added dropwise, and then the reaction mixture is stirred overnight. Afier adding water, the reaction mixture is evaporated and taken up in dichloromethane. The organic phase is separated off and dried over Mg504, filtered and concentrated to dryness. The residue is purified by chromatography over silica gel to yield a mixture of the title compounds (4-bromo-1 ,3-dimethyl-pyrazole and 4-bromo-1 ,5- dimethyl-pyrazole respectively in a ratio of 4:6).4-bromo-1 ,5-dimethyl-1H-pyrazole10331] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.41 (s, 1H),3.76 (s, 3H), 2.22 (s, 3H)4-bromo-1 ,3-dimethyl-1H-pyrazole10332] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.81 (s, 1H),3.74 (s, 3H), 2.09 (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 13808-64-5, its application will become more common.

Reference:
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 13808-64-5, These common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, 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.

10330] To a suspension of NaH 60% in oil (0.3 g; 7.45 mmol) in tetrahydrofuran (150 mE) there is added, at 100 C., 4-bromo-3-methyl-1H-pyrazole dissolved in 15 mE of tetrahydrofuran dropwise, over 15 minutes. Afier stirring for 40 minutes at ambient temperature, iodomethane (0.45 mE; 7.45 mmol) is added dropwise, and then the reaction mixture is stirred overnight. Afier adding water, the reaction mixture is evaporated and taken up in dichloromethane. The organic phase is separated off and dried over Mg504, filtered and concentrated to dryness. The residue is purified by chromatography over silica gel to yield a mixture of the title compounds (4-bromo-1 ,3-dimethyl-pyrazole and 4-bromo-1 ,5- dimethyl-pyrazole respectively in a ratio of 4:6).Step B: N-[4-[tert-Butyl(dimethyl)silyl]oxyphenyl]-1-methyl-pyrazol-4-amine To a solution of 30.8 g (0.137 mol) of the compound of Step A in 525 mL of anhydrous toluene there are successively added 29.8 g of sodium tert-butylate (0.310 mol), 4.55 g of Pd2(dba)3 (also referred to as tris(dibenzylideneacetone)dipalladium(0)) (4.96 mmol), 4.81 g of 2-di-tert-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (9.91 mmol) and 12.8 mL of 4-bromo-1-methyl-1H-pyrazole (0.124 mol). The batch is degassed under argon for 30 minutes and then refluxed for 3 hours. It is allowed to cool. The reaction mixture is concentrated to dryness and then taken up in dichloromethane, filtered over Celite and then concentrated to dryness again. The residue is then purified by chromatography over silica gel using dichloromethane and ethyl acetate as eluants to provide the expected product in the form of a solid.10333] The procedure is in accordance with Step B of Preparation 1?, replacing the 4-bromo-1 -methyl- 1H-pyra- zole by the mixture of isomers from Step A. A mixture of isomers in a ratio of 4:6 is obtained (respectively N-(4-{[tert- butyl(dimethyl)silyl]oxy}phenyl)-1 ,5-dimethyl- 1 H-pyrazol4-amine and N-(4-{ [tert-butyl(dimethyl)silyl]oxy}phenyl)1 ,3-dimethyl-1H-pyrazol-4-amine).

Statistics shows that 4-Bromo-3-methylpyrazole is playing an increasingly important role. we look forward to future research findings about 13808-64-5.

Reference:
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 13808-64-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13808-64-5, name is 4-Bromo-3-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATIVE EXAMPLE 15; Step A; N-methyl-4-bromopyrazole-3-carboxylic acid was prepared according to known methods, see: Yu. A. M.; Andreeva, M. A.; Perevalov, V. P.; Stepanov, V. I. ; Dubrovskaya, V. A.; and Seraya, V. l. in Zh. Obs. Khim, (Journal of General Chemistry of the USSR) 1982,52, 2592 (and the references cited therein) the disclosure of whichis incorporated hereinby reference thereto.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methylpyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/66147; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics