Category: 1062368-71-1

Electric Literature of 1062368-71-1, 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. 1062368-71-1, name is Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C9H7BrN2O2, 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.

n-Butyllithium (0.251 g, 3.92 mmol, 2.5 M in tetrahydrofuran) and dibutylmagnesium (1.629 g, 11.76 mmol, 1.0 M in heptane) were charged into a nitrogen filled three-necked flask at room temperature. A solution of methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate (2.000 g, 7.84 mmol) in tetrahydrofuran (25 mL) was added dropwise to the lithium tributylmagnesate complex (n-Bu3MgLi) solution at -25 C. and the mixture was stirred at -10 C. for 1 hour. The resulting mixture was added to a solution of sulfuryl dichloride (1.587 mL, 19.60 mmol) in toluene (20 mL) at -10 C. and the mixture was stirred for 20 minutes at -10 C. The organic solvents were removed by rotary evaporation to give a crude solid. Ammonium hydroxide (15 mL, 7.84 mmol) was added to the crude solid at room temperature, and the mixture was stirred for 15 minutes. After completion, the reaction mixture was concentrated to give crude title product. The crude material was purified by silica gel chromatography (25%-40% ethyl acetated in petroleum) to give crude (75% purity) product. The material was then purified by Prep-HPLC on a Gilson 281(PHG013) with Boston pHlex ODS column (21.2*250 mm, 10 m), using a gradient of acetonitrile (B) and 0.05% trifluoroacetic acid in water (A) at 35-55% B in 10 minute with stop at 15 minute, at a flow rate of 25 mL/minute to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 8.70 (dd, J=6.8, 1.0 Hz, 1H), 8.50 (s, 1H), 8.25 (dd, J=7.4, 1.0 Hz, 1H), 7.08 (t, J=7.1 Hz, 1H), 6.60 (s, 2H), 3.96 (s, 3H). MS (ESI+) m/z 256.1 (M+H)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1062368-71-1, Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (101 pag.)US2018/244640; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1062368-71-1, 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. 1062368-71-1, name is Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C9H7BrN2O2, 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.

n-Butyllithium (0.251 g, 3.92 mmol, 2.5 M in tetrahydrofuran) and dibutylmagnesium (1.629 g, 11.76 mmol, 1.0 M in heptane) were charged into a nitrogen filled three-necked flask at room temperature. A solution of methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate (2.000 g, 7.84 mmol) in tetrahydrofuran (25 mL) was added dropwise to the lithium tributylmagnesate complex (n-Bu3MgLi) solution at -25 C. and the mixture was stirred at -10 C. for 1 hour. The resulting mixture was added to a solution of sulfuryl dichloride (1.587 mL, 19.60 mmol) in toluene (20 mL) at -10 C. and the mixture was stirred for 20 minutes at -10 C. The organic solvents were removed by rotary evaporation to give a crude solid. Ammonium hydroxide (15 mL, 7.84 mmol) was added to the crude solid at room temperature, and the mixture was stirred for 15 minutes. After completion, the reaction mixture was concentrated to give crude title product. The crude material was purified by silica gel chromatography (25%-40% ethyl acetated in petroleum) to give crude (75% purity) product. The material was then purified by Prep-HPLC on a Gilson 281(PHG013) with Boston pHlex ODS column (21.2*250 mm, 10 m), using a gradient of acetonitrile (B) and 0.05% trifluoroacetic acid in water (A) at 35-55% B in 10 minute with stop at 15 minute, at a flow rate of 25 mL/minute to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 8.70 (dd, J=6.8, 1.0 Hz, 1H), 8.50 (s, 1H), 8.25 (dd, J=7.4, 1.0 Hz, 1H), 7.08 (t, J=7.1 Hz, 1H), 6.60 (s, 2H), 3.96 (s, 3H). MS (ESI+) m/z 256.1 (M+H)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1062368-71-1, Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (101 pag.)US2018/244640; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1062368-71-1, 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 1062368-71-1, name is Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 4-bromopyrazolo [1 ,5-ajpyridine-3-carboxylate (500 mg, 1.97 mmol), potassium trifluoro(2-methoxyethyl)borate (490 mg, 1.28 mmol), RuPhos (734 mg, 1.58 mmol), Pd(OAc)2(177 mg, 0.79 mmol) and C52CO3(1.92 g, 5.91 mmol) in CPME (8 mL) and water (2 mL) was stirred for 5 hours at 100 C under N2. The mixture was diluted with water,extracted with EA(x3), the organic layer was dried, concentrated. The crude product was purified via silica gel chromatography (PE-EA) to give desired compound as yellow solid (140 mg, 30%). ESI MS m/z = 235.3 [M+Hf.

According to the analysis of related databases, 1062368-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1062368-71-1 ,Some common heterocyclic compound, 1062368-71-1, molecular formula is C9H7BrN2O2, 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.

Methyl 4-bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (100 mg, 0.39 mmol), Pd(OAc)2 (5.3 mg, 0.024 mmol), BNAP (22 mg, 0.035 mmol) and Cs2CO3 (192 mg, 0.59 mmol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuum and argon), then toluene (2 mL) and morpholine (0.044 mL, 0.51 mmol) were added. Thereaction mixture was degassed again, and then was stirred at 120 C for 3 h. After cooled to rt, the reaction was filtered through a pad of CELITE, and the solvent was removed. The crude product was purified by reverse phase chromatography to provide Intermediate 109 (74 mg, 72%) as a light tan solid. ?H NMR (400MHz, CDC13) oe 8.46 (s, 1H), 8.43 (d, J=6.6 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 7.05 (t, J7.2 Hz, 1H), 4.11 – 4.04(m, 4H), 3.94 (s, 3H), 3.40 – 3.27 (m, 4H). LC-MS(ESI) m/z: 262.0 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1062368-71-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1062368-71-1 ,Some common heterocyclic compound, 1062368-71-1, molecular formula is C9H7BrN2O2, 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.

Methyl 4-bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (100 mg, 0.39 mmol), Pd(OAc)2 (5.3 mg, 0.024 mmol), BNAP (22 mg, 0.035 mmol) and Cs2CO3 (192 mg, 0.59 mmol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuum and argon), then toluene (2 mL) and morpholine (0.044 mL, 0.51 mmol) were added. Thereaction mixture was degassed again, and then was stirred at 120 C for 3 h. After cooled to rt, the reaction was filtered through a pad of CELITE, and the solvent was removed. The crude product was purified by reverse phase chromatography to provide Intermediate 109 (74 mg, 72%) as a light tan solid. ?H NMR (400MHz, CDC13) oe 8.46 (s, 1H), 8.43 (d, J=6.6 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 7.05 (t, J7.2 Hz, 1H), 4.11 – 4.04(m, 4H), 3.94 (s, 3H), 3.40 – 3.27 (m, 4H). LC-MS(ESI) m/z: 262.0 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1062368-71-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem