Day: March 17, 2022

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. 847406-13-7, name is Ethyl 1-(5-bromopyridin-3-yl)piperidine-4-carboxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 847406-13-7

To a flask was added 7A (1. 00 G, 3.19 MMOL), DIOXANE (13 ML), triethyl AMINE (0. 97 g, 9. 58 mmol) and pinacol borane (0. 613 G., 4. 79’mmol). The mixture was degassed with N2 for 15 min and Pd2Cl2- (dppf) dcm (0.132 g, 0.16 mmol) was added. The flask was heated to 90C for 12 h and cooled to ambient temperature. The crude product was concen- rated in vacuo and purified by flash chromatography on silica gel eluting with 15% 7N methanolic ammonia/CM to provide the title compound (400 mg, 45%) 1H NMR (DMSO-d6, 400 MHz) 5 8.31 (d, J=2.73 Hz, 1H), 8.09 (m, 1H), 7.18 (m, 2H), 4.16 (dd, J=7.02, 14.04 Hz, 2H), 3.67 (m, 2H), 2. 85 (m, 2H), 2.46 (m, 1H), 2.05 (m, 2H), 1.89 (m, . 2H), 1.28 (t, J=7. 21 HZ,. 3H).

The synthetic route of 847406-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOS CORPORATION; WO2005/19200; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 917364-11-5, 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.917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, molecular weight is 166.18, as common compound, the synthetic route is as follows.

Step (a) 5,6,7,8-Tetrahydroimidazo[l,2-alpha]pyridin-2-ylmethanol5,6,7,8-Tetrahydroimidazo[l,2-«]pyridine-2-carboxylic acid (230 mg, 1.38 mniol) was suspended in THF (2.287 mL) and borane-tetrahydrofyuran complex (6.92 mL, 6.92 mmol) was added. The mixture was heated at reflux for 3 h then cooled to room temperature over a period of two days, then heated to reflux for a further 16 h. Methanol (10 mL) was then added dropwise and the reaction stirred for one hour then concentrated in vacuo. The crude product was dissolved in methanol (5 mL) and passed through an SCX column washing with methanol (100 mL) and eluting with 3.5N ammoniacal methanol (75 mL). The basic organic layer was concentrated to give the sub-title compound as a yellow oil (134 mg). 1H NMR (400 MHz, CDCl3) delta 6.72 (s, IH), 4.55 (s, 2H), 3.91 (t, J = 5.9 Hz, 2H), 2.85 (t, J = 6.3 Hz, 2H), 2.01 – 1.87 (m, 4H).

Statistics shows that 917364-11-5 is playing an increasingly important role. we look forward to future research findings about 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, 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, 87674-21-3, blongs to pyridine-derivatives compound. HPLC of Formula: C7H6FNO

To a stirred solution of 3-fluoro-4-acetylpyridine (5.3 g, 38.1 mmol) in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60 C. for 2.5 hour. This solution was cooled down and ethylacetate (70 mL) was added. After 30 minutes of stirring, the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g). 1H NMR (DMSO-d6/400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87674-21-3, its application will become more common.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142415; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65873-72-5, 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. 65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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.

A stirred solution of 6-methoxy-3-pyridmecarboxaldehyde (0.45g, 3.3mMol) in 3N HCl(1OmL) was heated to 1000C for 30 minutes. Upon cooling, needle-like crystals developed. The crystals were collected via filtration to yield 17-2. 1H-NMR (CD3OD) delta 9.64 (s, IH), delta 8.17-8.16 (m, IH), delta 7.96-7.94 (m, IH), delta 6.58(d, IH).

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 65873-72-5, 6-Methoxynicotinaldehyde.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116026-95-0 ,Some common heterocyclic compound, 116026-95-0, molecular formula is C11H14N2O3, 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.

(4-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (100 mg) was dissolved in a hydrochloric acid-methanol solution (2.0 ml), and the solution was stirred under reflux for 30 min. The solvent was removed by distillation under the reduced pressure. 1-Chloro-propan-2-one (42 mg) dissolved in a 5 N aqueous sodium hydroxide solution (0.5 ml) was added to the residue, and the mixture was allowed to stand in an airtightly stoppered state for two days. The reaction mixture was neutralized with 10% hydrochloric acid, and dichloromethane was then added thereto for extraction. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-acetone system to give 2-methyl-[1,7]naphthyridin-3-ol (22 mg, yield 31%). 2-Methyl-[1,7]naphthyridin-3-ol (22 mg), 4-chloro-6,7-dimethoxyquinoline (92 mg), and 4-dimethylaminopyridine (50 mg) were suspended in 1,2-dichlorobenzene (1.5 ml), and the suspension was stirred at 140C for 8.5 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-methanol system to give the title compound (25 mg, yield 53%). 1H-NMR (CDCl3, 400 MHz): delta 2.76 (s, 3H), 4.01 (s, 3H), 4.06 (s, 3H), 6.54 (d, J = 5.6 Hz, 1H), 7.44 (s, 1H), 7.49 (s, 1H), 7.52 (d, J = 6.0 Hz, 1H), 7.61 (s, 1H), 8.57 (m, 2H), 9.45 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 348 (M+1)+ (4-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (100 mg) was dissolved in a hydrochloric acid-methanol solution (2.0 ml), and the solution was stirred under reflux for 30 min. The solvent was removed by distillation under the reduced pressure. 2-Chloro-1-phenyl-ethanone (70 mg) dissolved in a 5 N aqueous sodium hydroxide solution (0.6 ml) was then added to the residue, and the mixture was allowed to stand in an airtightly stoppered state for two days. The reaction solution was neutralized with 10% hydrochloric acid, and dichloromethane was then added thereto for extraction. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-acetone system to give 2-phenyl-[1,7]naphthyridin-3-ol (3 mg, yield 3%). 2-Phenyl-[1,7]naphthyridin-3-ol (3 mg), 4-chloro-6,7-dimethoxyquinoline (9 mg), and 4-dimethylaminopyridine (5 mg) were suspended in 1,2-dichlorobenzene (1.0 ml), and the suspension was stirred at 140C for 9 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-methanol system to give the title compound (3 mg, yield 54%). 1H-NMR (CDCl3, 400 MHz): delta 4.00 (s, 3H), 4.07 (s, 3H), 6.59 (d, J = 5.6 Hz, 1H), 7.39 (m, 4H), 7.61 (m, 2H), 7.86 (s, 1H), 7.98 (m, 2H), 8.50 (d, J = 5.6 Hz, 1H), 8.64 (d, J = 5.6 Hz, 1H) 9.62 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 432 (M+Na)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116026-95-0, its application will become more common.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 73177-35-2, Adding some certain compound to certain chemical reactions, such as: 73177-35-2, name is 2-Methyl-1H-pyrrolo[3,2-b]pyridine,molecular formula is C8H8N2, 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 73177-35-2.

Example 2 (see general route 2, procedure E, F, C and D)2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-N-(2-methoxypyridin- 4-yl)-2-oxoacetamide (3) [00252] To a solution of 2-methyl-lH-pyrrolo[3,2-b]pyridine (74.4 mg, 0.563 mmol) and 4-chlorobenzyl chloride (0.0780 mL, 0.619 mmol) in DMSO (8 mL) at room temperature was added powdered potassium hydroxide (69.5 mg, 1.24 mmol). The reaction was stirred at room temperature for 12 hours, after which LCMS analysis indicated that the reaction was complete. The reaction mixture was diluted in water and extracted with dichloromethane (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a clear residue. Purification was achieved by silica gel chromatography using 30 to 90% ethyl acetate in hexanes over 80 minutes affording l-(4-chlorobenzyl)-2 -methyl- lH-pyrrolo[3,2-b]pyridine (64.2 mg, 0.250 mmol, 44% yield) as an off-white solid. NMR (400 MHz, CDC13) delta (ppm): 8.41 (dd, 1H), 7.41 (d, 1H), 7.24 (d, 2H), 7.01 (dd, 1H), 6.86 (d, 2H), 6.54 (s, 1H), 5.27 (s, 2H), 2.41 (s, 3H).[00253] To a solution of l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridine (341 mg, 1.33 mmol) in dichloromethane (25 mL) was added aluminum trichloride (886 mg, 6.65 mmol). The mixture was stirred at room temperature for 20 minutes, after which ethyl oxalyl chloride (0.744 mL, 6.65 mmol) was added. The reaction mixture was stirred at room temperature for an additional three hours, after which it was poured over ice and extracted with ethyl acetate (3 x 50 mL), dried (sodium sulfate) filtered and concentrated to afford 2-(l- (4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetic acid (76.5 mg, 0.233 mmol, 18% yield) an off-white solild. This material was used without any purification in the next step. The intended product of this reaction, ethyl 2-(l-(4-chlorobenzyl)-2-methyl-lH- pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetate, was observed in trace amounts and was not isolated from the reaction mixture. NMR (400 MHz, CDC13) delta (ppm): 8.44 (dd, 1H), 7.41 (dd, 1H), 7.20 (d, 2H), 7.04 (dd, 1H), 6.84 (d, 2H), 6.54 (s, 1H), 5.27 (s, 2H), 2.77 (s, 3H)[Carboxylic acid proton not detected in 1H NMR]. LCMS: 2.18 min, [ES]” found 327.10.[00254] To a solution of 2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3- yl)-2-oxoacetic acid (76.5 mg, 0.218 mmol) in acetonitrile (7 mL) was added triethylamine (0.304 mL, 2.18 mmol), 2-methoxypyridin-4-amine (29.8 mg, 0.240 mmol), followed by a 50% ethyl acetate solution of T3P (972 mg, 1.53 mmol). The reaction was heated to 60 C for 2 hours, after which additional triethylamine (0.304 mL, 2.18 mmol) and T3P solution (972 mg, 1.53 mmol) were added. The reaction mixture was stirred at 60 C for 12 hours, after which it was diluted in water, extracted with ethyl acetate (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography (Luknova 40g, 20 mL/min) using 10 to 60% ethyl acetate in hexanes over 60 minutes. 2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-N-(2- methoxypyridin-4-yl)-2-oxoacetamide (31 mg, 0.071 mmol, 33% yield) was isolated as a light-tan solid. NMR (400 MHz, CDC13) delta (ppm): 12.5 (br. s, IH), 8.55 (dd, IH), 8.08 (d, IH), 7.55 (dd, IH), 7.23-7.29 (m, 4H), 7.18 (dd, IH), 6.87 (d, 2H), 5.34 (s, 2H), 3.90 (s, 3H), 2.70 (s, 3H).

According to the analysis of related databases, 73177-35-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 722550-01-8, 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 722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (70 mg, 0.24 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 4a (39 mg, 0.24 mmol) in acetone (3 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration, washed with acetone, and dried under reduced pressure to afford 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1 ,2-a]pyridine hydrobromide 5a (45 mg, 43%) as a pink solid. 1H NMR (300 MHz, DMSO-d6) . delta 13.03 (s, 1H), 8.50 (d, J = 7.6 Hz, 1H). 8.20 (s, 1H), 7.89 (s, 1H), 6.97 (s, 1H), 6.95 (dd, J=2.2, 7.6 Hz, 1H), 6.30 (d, J= 2.0 Hz, 1H), 4.05 (s, 3H), 3.99 (s, 3H). 3.48-3.38 (m, 4H), 2.08- 1.98 (m, 4H); HPLC ( Method 4) 98.7% (AUG), tR = 19.02 min. APCI MS m/z 358 [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 722550-01-8, 4-(Pyrrolidin-1-yl)pyridin-2-amine.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, 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 73406-50-5.

2-(pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine 18 g (0.093 moles) of ethyl-3-hydroxypicolinate [J. Heterocyclic Chem. 23, 665, 1986] were cooled at -5 C. and ml 250 of pyrrolidine were added under nitrogen atmosphere. After the addition, the solution was allowed to reach room temperature, stirred 24 h and then evaporated in vacuo to give 15 g of the title compound as a slight yellow oil which crystallized on standing.

According to the analysis of related databases, 73406-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dr. L. Zambeletti SpA; US5089507; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206968-88-8, 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.1206968-88-8, name is (5-Bromo-3-chloropyridin-2-yl)methanol, molecular formula is C6H5BrClNO, molecular weight is 222.467, as common compound, the synthetic route is as follows.

DMP (45.83g, 102.lOmmoI) was added portion wise to a stirred solution of (5-bromo-3-chloropyridin-2-yl)-methanol (16g, 72.O7mmoI) in DCM (320mL) at 0C and stirred for 16h at RT. The RM was filtered through celite and washed with DCM (3x100mL).The filtrate was washed with Aq.NaHCO3 (200mL), water (200mL), brine(250mL), dried (Na2SO4), filtered, concentrated under reduced pressure to give crude. The crude was purified by CC (0-5% EtOAc in PE) to give 5-bromo-3-chloropicolinaldehyde (lOg, 66%) as light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 1206968-88-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 2604-39-9 , The common heterocyclic compound, 2604-39-9, name is 2-Chloro-5-nitropyridin-4-amine, molecular formula is C5H4ClN3O2, 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.

NBS (564 mg, 3.17 mmol) was added to a solution of 1 (500 mg, 2.88 mmol) in 8 mL of AcOH. The resulting mixture was stirred at 60 C for 4 h. After cooled to room temperature, the mixture was diluted with water. The precipitate was collected by filtration to afford 580 mg of 2 as a yellow solid, which was used in the next step without further purification. [M+Hj : 251.91, 253.96.

The synthetic route of 2604-39-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; ZHANG, Dengyou; ZHENG, Canhui; CHEN, Zhuo; LIU, Liu; HUANG, Liyue; YANG, Chao-Yie; (110 pag.)WO2018/213211; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem