Month: July 2021

Synthetic Route of 6000-50-6, 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 6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-(4-aminophenyl)-4-{1-[(4-methylphenyl)sulfonyl]-1H-indol-5-yl}pyridazin- 3(2H)-one (200 mg, 0.438 mmol) in dichloromethane (16.2 mL) and N,N-dimethylformamide (4.00 mL) was added pyridine (71.0 muL, 0.876 mmol) followed by portion wise addition of 4- nitrophenyl carbonochloridate (106 mg, 0.526 mmol) over 1 minute, and the reaction mixture stirred at r.t. for1 hour. To this reaction mixture was added N,N-diisopropylethylamine (381 muL, 2.19 mmol) followed by 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (169 mg, 0.876 mmol) under argon and the reaction mixture stirred at r.t. for 16 hours. The reaction mixture was combined with another batch (0.219 mmol), and concentrated to give a residue. The crude residue was triturated with water-ethanol and the resulting precipitate collected by filtration, washed with ethyl acetate, diethyl ether and dried to give 246 mg (90% purity,63% combined yield over two steps) of the desired product as pale yellow solid. (0981) LC-MS (Method 5): Rt = 0.85 min; MS (ESIpos): m/z = 603 [M+H]+ (0982) 1H-NMR (400 MHz, DMSO-D6) delta (ppm): 2.29 (s, 3H), 4.80 (d, 4H), 6.90 (s, 1H), 7.37 (d, 2H), 7.53-7.54 (m, 1H), 7.60-7.66 (m, 2H), 7.83-7.97 (m, 5H), 8.10 (s, 2H), 8.24 (s, 1H), 8.53- 8.55 (m, 1H), 8.63-8.65 (m, 2H).

According to the analysis of related databases, 6000-50-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17880-61-4, 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 17880-61-4, name is Methyl 5-ethynylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Sodium 5-[4′-(4′-aminophenyl)buta-1 ‘,3’-diyn-1 -yl]pyridine-2-carboxylate (144): Copper (II) acetate (1 .36 g, 7.46 mmol, 2.0 equiv) is added at room temperature under stream of argon to a stirred solution of 142 (0.60 g, 3.73 mmol) and 4- ethylnylbenzenamine (2.18 g 18.63 mmol, 5.0 equiv) dissolved in anhydrous pyridine (10 mL) and MeOH (10 mL). The reaction mixture is stirred at room temperature for 20 h. The resulting suspension is filtered, and the solid is washed with EtOAc (3^50 mL). The solid is dried under high vacuum for 12 h to afford as an orange powder, and then used for next step directly. 4N NaOH (10 mL) is added to a stirred solution of the crude methyl ester (600 mg) in MeOH (50 mL) at room temperature. Then reaction solution is heated to reflux for 40 min under argon. The reaction mixture turned clear. After all the starting material has been consumed monitored by TLC,the reaction mixture is cooled to room temperature, and the solvents are removed by evaporation under reduced pressure. The yellow solid is washed by water (3^50 mL), EtOAc (3×50 mL) to give a yellow solid (320 mg, 31 % yield, for two steps ), which is used for next step without future purification. 1 H NMR (300 MHz, CD3OD) 56.62 (d, J=8.4 Hz, 2H), 7.26 (d, J=8.7 Hz, 2H), 7.59 (d, J=9.0 Hz, 1 H), 8.27 (d, J=10.2 Hz, 1 H), 9.01 (s, 1 H); 13C NMR (75 MHz, CD3OD) 570.50, 75.996, 78.48, 85.59, 107.59, 1 14.17, 127.44, 133.09, 134.06, 137.62, 142.94, 150.69, 170.58; MS (ESI, positive): m/z 263 [M+H+].

According to the analysis of related databases, 17880-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DUKE UNIVERSITY; ZHOU, Pei; TOONE, Eric, J.; WO2012/31298; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 130658-65-0 ,Some common heterocyclic compound, 130658-65-0, molecular formula is C10H14N2O, 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 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline used as a starting material was prepared as follows:- Diethyl azodicarboxylate (3 ml) was added over 15 minutes to a stirred mixture of 1-(4-pyridyl)piperidin-4-ol (3.39 g), 3-(N-tert-butoxycarbonylamino)phenol (Chemical Abstracts, vol. 119, abstract 139113; PCT Patent Application WO 9306085; 3.98 g), triphenylphosphine (4.99 g) and THF (150 ml) which had been cooled to 4 C. The resultant mixture was stirred for 48 hours at ambient temperature. The solvent was evaporated and the residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant foam was crystallized from diethyl ether to give tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate (4.65 g), m.p. 165-166 C. A 2.2M solution of hydrogen chloride in methanol (45 ml) was added over 15 minutes to a stirred solution in methanol (25 ml) of a portion (2.53 g) of the carbamate so obtained. The mixture was stirred at ambient temperature for 24 hours. The solvent was evaporated and the residue was dissolved in water (50 ml). A 1M aqueous sodium hydroxide solution (25 ml) was added and the mixture was stirred for 1 hour. The precipitate was collected, washed with water and with diethyl ether and dried. There was thus obtained 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline (1.71 g), m.p. 184-186 C.; NMR Spectrum 1.60 (m, 2H), 1.96 (m, 2H), 3.23 (m, 2H+H2O), 3.65 (m, 2H) 4.48 (m, 1H), 5.00 (s, 2H), 6.16 (m, 3H), 6.82 (d, 2H), 6.88 (t, 1H), 8.15 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130658-65-0, its application will become more common.

Reference:
Patent; ZENECA LIMITED; US2003/207882; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1152617-24-7 ,Some common heterocyclic compound, 1152617-24-7, molecular formula is C5H4ClIN2, 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.

To a mixture of Z l7c (6.95 kg, assay 72%, 27.23 mol) in l,4-dioxane (72 L) was added Xantphos (233 g, 41 1 mmol, 0.015 eq), Pd2(dba)3 (186 g, 206 mmol,0.0075eq), Z l7b (7.13 kg, 28.02 mol) and DIPEA (7.02 kg, 54.46mol). The system was vacuated and purged with nitrogen gas three times. The mixture was stirred at 65 C for 16 h under N2. The mixture was cooled to rt and water (50 L) was added, filtered. The cake was washed with EA (25L). The filtrate was extracted with EA (4 x 20 L). The organic phase was concentrated in vacuum to offer the crude product which was combined with the cake. Then DCM (60 L) was added to the crude product and stirred at 25-30C for 18h and then filtered. The filter cake was slurried with CH2CI2 (30 L) for 4 hrs and filtered. The filter cake was slurred in CH2CI2 (30 L) for 16 hrs and filtered. Then the filter cake was dried in vacuum to give Z17a (9.1 kg, 84 %) as light yellow solid. NMR (400 MHz, DMSO-d6)5 = 7.89 (s, 1H), 7.7 (d, J = 7.6 Hz, 1H), 7.18 (bs, 2H), 6.40 (bs, 2H), 5.97 (d, J = 7.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1152617-24-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131803-48-0, 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. 131803-48-0, name is Methyl 6-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, 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.

Methyl 6-(anilinomethyl)pyridine-3-carboxylate hydrochloride (I-30) A mixture of N-Boc-aniline (350 mg, 1.81 mmol) and methyl 6-(bromomethyl)pyridine-3-carboxylate (500 mg, 2.17 mmol) in THF (10 mL) at 0 C. was added with sodium hydride (108 mg, 60% dispersion in mineral oil, 2.71 mmol). The reaction was stirred for 1 h at room temperature was then heated at 60 C. for 5 h. The reaction was cooled to room temperature and quenched with water. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic phase was washed with brine, dried over MgSO4 then evaporated to dryness. The residue was taken up with 4N solution of HCl in dioxane (5.5 mL) and the resulting mixture was stirred at room temperature for 2 h. The reaction was concentrated under reduced pressure and the residue was triturated with diethyl ether to provide the title compound (394 mg, 78%) as an off-white solid. 1H NMR (400 MHz, DMSO): delta 9.07 (d, J=2.0 Hz, 1H), 8.33 (dd, J=2.0, 8.0 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.14-7.10 (m, 2H), 6.74-6.70 (m, 3H), 4.54 (s, 2H), 3.88 (s, 3H), NH not observed.

According to the analysis of related databases, 131803-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POEL, Herve; WHITTAKER, Ben; US2015/158858; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256810-58-8, 6-Bromo-3-chloro-2-methoxypyridine, 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, Recommanded Product: 6-Bromo-3-chloro-2-methoxypyridine, blongs to pyridine-derivatives compound. Recommanded Product: 6-Bromo-3-chloro-2-methoxypyridine

Reference Example 4-15 (5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one (600 mg, synthesized according to Tetrahedron Asymmetry, 1995, 239 using dimethyl (R)-glutamate hydrochloride as a raw material) in acetonitrile (6 mL) was added to a solution of 6-bromo-3-chloro-2-methoxypyridine (667 mg), bis(triphenylphosphine)palladium(II) dichloride (81 mg) and copper iodide (22 mg) in triethylamine (12 mL) in a nitrogen gas stream at 40 C. over 30 minutes. The mixture was stirred at room temperature for four hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1?0:1) to give the title compound as a colorless oil (452 mg, 52%). 1H NMR (300 MHz, CDCl3) delta ppm 2.12-2.48 (m, 3H), 2.53-2.70 (m, 1H), 3.79 (s, 3H), 3.80 (s, 3H), 4.04 (s, 3H), 4.26 (d, J=15 Hz, 1H), 4.37-4.46 (m, 1H), 4.89 (d, J=15 Hz, 1H), 6.38-6.49 (m, 2H), 6.94 (d, J=7.8 Hz, 1H), 7.18-7.25 (m, 1H), 7.57 (d, J=7.8 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256810-58-8, 6-Bromo-3-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1065267-14-2, (3,5-Difluoropyridin-2-yl)methanol, 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, 1065267-14-2, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(3,5-Difluoropyridin-2-yl)methyl 4-methylbenzenesulfonate (I-5)To a solution of (3,5-difluoropyridin-2-yl)methanol (0.25 g, 0.7 mmol) in tetrahydrofuran (THF; 10 mL) was added potassium hydroxide (KOH; 0.14 g, 2.55 mmol) at RT, and the mixture was stirred for 15 min p-Toluenesulfonyl chloride (0.42 g, 2.21 mmol) was added slowly at RT, and the reaction mixture was stirred for another 18 h. After complete consumption of the starting material (by TLC), the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 15% EtOAc/hexane afforded compound I-5 (0.18 g, 0.25 mmol, 35%) as colorless liquid. 1H NMR (500 MHz, CDCl3): delta 8.29 (s, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.20-7.16 (m, 1H), 5.20 (s, 2H), 2.45 (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,1065267-14-2, its application will become more common.

Reference:
Patent; Viamet Pharmaceuticals, Inc.; US2012/329788; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. A new synthetic method of this compound is introduced below., Recommanded Product: 4-Benzyloxy-2-(1H)-pyridone

A mixture of N,N-diethyl-7-iodopyrazolo[1,5-a]pyridin-3-amine (0.25 g, 0.79 mmol), 4-benzyloxy-2(1H)-pyridone (0.19 g, 0.94 mmol), copper(1) iodide (0.003 g, 0.016 mmol) and potassium carbonate (0.13 g, 0.94 mmol) in DMF (5.0 ML) was heated at 150 C. for 3 h and cooled down to room temperature.The mixture was partitioned between EtOAc and H2O and separated.The organic layer was concentrated in vacuo to dryness.The residue was subjected to column chromatography (E:H=1:4) to give 0.18 g (60%) of a clear oil as the title compound: 1H NMR (400 MHz, CDCl3) delta 7.96 (d, J=5.8 Hz, 1H), 7.81 (s, 1H), 7.48-7.43 (m, 6H), 7.12-7.08 (m, 1H), 6.80 (s, 1H), 6.74 (d, J=5.8 Hz, 1H), 6.59 (d, J=6.4 Hz, 1H), 5.19 (s, 2H), 3.14 (q, J=7.1 Hz, 4H), 1.06 (t, J=7.1 Hz, 6H); MS (EI) m/z 389.25 (M++H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; Fu, Jian-Min; US2004/2511; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15862-34-7, Adding some certain compound to certain chemical reactions, such as: 15862-34-7, name is 5-Bromo-2-hydroxy-3-nitropyridine,molecular formula is C5H3BrN2O3, 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 15862-34-7.

To a round-bottom flask charged with 5-Bromo-3-nitro-pyridin-2-ol (976 mg, 4.0 mmol) was added 6.0 mL of phosphoryl chloride, the resulting suspension was heated to 105 0C and kept for 12 hrs. Then the excess POCI3 was removed under reduced pressure, the residue then was dissolved in anhydrous 10 mL of DCM, 1 mL of 3-aminopropyl-1-ol was then added. The resulting mixture was stirred for 30 min., DCM was then removed under reduced pressure to give a oil residue which was stirred at 45 0C for 12 hrs. Then the reaction was quenched with water, extracted with ethyl acetate, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was obtained as a yellow solid 3-(5-bromo-3-nitro-pyridin-2-ylamino)-propan-1-ol and was used for next step without further purification. 1H NMR (400 MHz, CDCI3) delta 1.90 (2H, m), 2.60 (1 H, br.), 3.71 (2H, m), 3.78 (2H, m), 8.42 (1 H, d, J = 2.4 Hz), 8.55 (1 H, d, J = 2.4 Hz); MS m/z (MH)+: 276, 278

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. 15862-34-7, 5-Bromo-2-hydroxy-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; S*BIO PTE LTD; YU, Niefang; WO2006/101456; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 286946-77-8 ,Some common heterocyclic compound, 286946-77-8, molecular formula is C5H3BrClNO, 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.

To a solution of 65 5-bromo-2-chloropyridin-3-ol (50.2 g, 241 mmol) in 56 N,N-dimethylformamide (200 mL) were added successively 66 benzyl bromide (33.0 mL, 278 mmol) and 67 potassium carbonate (48.6 g, 352 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction solution was added 14 water (600 mL), and the mixture was stirred for 2 hr. The precipitate was collected by filtration, and dried under reduced pressure to give 68 3-(benzyloxy)-5-bromo-2-chloropyridine (69.7 g, yield 96%). 1H-NMR (DMSO-D6) delta: 5.29 (2H, s), 7.33-7.47 (5H, m), 7.98 (1H, d, J=2.1 Hz), 8.14 (1H, d, J=1.8 Hz)

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. 286946-77-8, 5-Bromo-2-chloropyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JAPAN TOBACCO INC.; NAGAMORI, Hironobu; NISHIMARU, Tatsuya; TAKAGI, Masaki; MITANI, Ikuo; NAKAGAWA, Yuichi; US2019/152926; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem