Category: 153747-97-8

Synthetic Route of 153747-97-8, Adding some certain compound to certain chemical reactions, such as: 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H20BrN3O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 153747-97-8.

To a stirred solution of tert-butyl 4-(5-bromo-2-pyridyl)piperazine-1-carboxylate (3 g, 8.77mmol) in dioxane (30 mL), 4 N HCl in dioxane (10 mL) was added at RT and stirred for 4 h(TLC indicated complete consumption of starting material). EtOAc (50 mL) was added to thereaction mixture, stirred for 30 min., the solid was filtered, washed with ether (20 mL) anddried under reduced pressure to afford 1-(5-bromo-2-pyridyl)piperazine hydrochloride (2.1 g,93%) as an off-white solid. LCMS (ESI+ ): m/z: 242.43 [M+Ht.

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153747-97-8 ,Some common heterocyclic compound, 153747-97-8, molecular formula is C14H20BrN3O2, 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.

The gaseous trifluororacetaldehyde was trapped with the dry ice-filled cold finger and dripped into a THF solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (1 g, 2.92 mmol) with 2.5 M n-butyllithium in hexanes (1.29 mL, 3.2 mmol) at -78 C under nitrogen atmosphere. After addition, the reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was quenched with saturated ammonium chloride aqueous solution at -78 0C and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford a light yellow solid. The crude material was purified by flash chromatography on silica gel, eluting with 10 – 80% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford a colorless sticky solid (450 mg, 35.9% yield). The Boc protected titled compound (200 mg, 0.466 mmol) was stirred in 50% TFA in DCM (5 mL) for 10 min. The reaction mixture was concentrated to afford the titled product as a TFA salt (150 mg, yield 98%). MS (m/z, MH+): meas. 330.0 calc. 329.25

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. 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 153747-97-8, blongs to pyridine-derivatives compound. Product Details of 153747-97-8

To a solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (250 mg, 0.73 mmol) in 3.5 mL anhydrous THF was added 1.6 M /j-butyllithium (500 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 min, the reaction mixture was charged with oxetan-3-one (131 mg, 1.82 mmol) in 200 muL DCM. The reaction mixture was stirred at -78 0C for 2 h and at room temperature for 16 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 – 100% EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford a off white solid (80 mg, 32.7% yield). The Boc protected title compound (140 mg, 0.417 mmol) was dissolved in DCM and charged with lutidine (194 muL, 1.67 mmol). The reaction mixture was cooled at 0 0C, charged with trimethylsilyl trifluoromethanesulfonate (1.25 mmol, 228 uL) and stirred at 0 0C for 2 h. The reaction mixture was poured into ice and the mixture was partitioned between DCM and water. The organic layer was dried over Na2SO4 and concentrated to afford a brown greasy solid (70 mg, yield 71%). MS (m/z, MH+): meas. 236.4 calc. 236.3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 153747-97-8, blongs to pyridine-derivatives compound. Computed Properties of C14H20BrN3O2

General procedure: A reaction tube was charged with benzenesulfonyl fluorideboronic acid 3 (61 mg, 0.30 mmol, 1.5 equiv), Pd(OAc)2 (2.3 mg, 0.010 mmol, 5.0 mol %) and XPhos (9.5 mg, 0.020 mmol, 10 mol %), sealed with a rubber septum, evacuated and back-filled with N2 three times. Degassed 1,4-dioxane (0.8 mL), degassed 1.0 M aq. K3PO4 solution (0.4 mL, 0.40 mmol, 2.0 equiv) and aryl halide* (0.20 mmol, 1.0 equiv) were added subsequently, and the reaction mixture stirred under positive pressure of N2 in a preheated aluminium heating block at 40 C for 4 h (5a, b, f, g, h, l), 6 h (5c, d, e, i, j, m) or 24 h (5k). After cooling to ambient temperature, the reaction mixture was diluted with EtOAc, dried with anhydrous MgSO4, filtered over Celite and concentrated in vacuo. The crude product was purified by flash column chromatography to afford the biarylsulfonyl fluoride. *In the case where aryl halide is a solid, it was added to the vessel before evacuating and back-filling.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Article; Lou, Terry Shing-Bong; Willis, Michael C.; Tetrahedron; vol. 76; 1; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

The compound (R)-N,N-bis(tert-butoxycarbonyl)-3-(1-(2-chloro-3,6-difluorophenyl)ethoxy)-5-(4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.89 g, 1.46 mmol)Dissolved in DME (10 mL),Then, tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.46 mmol) was added to the reaction mixture.Cesium carbonate (1.43g, 4.38mmol),Water (2mL) andPd(dppf)Cl2.CH2Cl2 (120 mg, 0.15 mmol).After the reaction system was purged with nitrogen (nitrogen) three times,Stir at 100C overnight,Then add ethyl acetate (50 mL)Diluted the reaction solution with water (12 mL).The layers were separated, the aqueous phase was extracted with ethyl acetate (50 mL x 2), and the combined organic phases were washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether (v/v) = 1/1)The title compound was obtained as a yellow oil (0.69 g, 63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.Application In Synthesis of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

To a stirred solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (10 g, 29.21 mmol) in 1,4-dioxane (50mL), 4N HCI solution in dioxane (100 mL, 10V) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residue was washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, 1 H), 7.82 (dd, J = 9.2, 2.4 Hz, 1 H), 6.99 (d, J = 9.2 Hz, 1 H), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 min, 99.3 % (Max).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153747-97-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step II: tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (Intermediate 1-XIII) A mixture of 1-11 (4.30 g, 12.57 mmol), bis(pinacolato)diboron (3.82 g, 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100 C. for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (50 mL*3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1-XIII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98%) as a yellow solid; LCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M++1].

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (132 pag.)US2017/8885; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

A mixture of 1-28 (4.30 g, 12.57 rnmol), bis(pinacolato)diboron (3.82 g, 15.07 mmcl) and KOAc (2.94 g, 37.69 mmcl) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocenepalladium(II) dichloridedichloromethane complex (0.307 g, 0.376 mmcl), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate(50 mL x 3) . The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1-CII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98%) as a yellow solid; IJCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M+1].

With the rapid development of chemical substances, we look forward to future research findings about 153747-97-8.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; NAIK, Keshav; SALUNKHE, Videsh; KULKARNI, Rakesh; PARDESHI, Vishwajeet; BHUNIYA, Debnath; KULKARNI, Bheemashankar; MOOKHTIAR, Kasim Abbaas; (274 pag.)WO2017/38909; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153747-97-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert -butyl 4-(5-bromopyridin-2-yl)piperazine-l-carboxylate (250 mg, 0.730 mmol) in 2.5 mL anhydrous THF was added 2.5 M w-butyllithium (320 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 mins, the reaction mixture was charged with dimethyl phosphinic chloride (164.4 mg, 1.46 mmol) in 1 mL anhydrous THF. The reaction mixture was warmed to -30 0C over 3 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 – 100% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford an off white solid (100 mg, 40.3% yield). The Boc protected title compound was dissolved in 2-PrOH (1 mL) and charged with 4 N HCl. The reaction mixture was heated at 70 0C for 30 min, and concentrated to afford the titled product as a HCl salt. MS (m/z, MH+): meas. 240.2 calc. 240.3

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem