Category: pyridine-derivatives

Electric Literature of 6231-18-1 ,Some common heterocyclic compound, 6231-18-1, molecular formula is C7H9NO2, 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.

General procedure: To a stirred cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (1.0 mL, 6.0 mmol) in THF (5 mL) were added BuLi (1.6 M hexanes solution, 6.0 mmol) and, 5 min later, FeBr2 (0.43 g, 2.0 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (2.0 mmol). After 2 h at room temperature, the electrophile (6.0 mmol) was added. The mixture was stirred for 1 h before addition of H2O (10 mL) and extraction with EtOAc (3¡Á20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure.

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. 6231-18-1, 2,6-Dimethoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nagaradja, Elisabeth; Chevallier, Floris; Roisnel, Thierry; Jouikov, Viatcheslav; Mongin, Florence; Tetrahedron; vol. 68; 14; (2012); p. 3063 – 3073;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86649-57-2, 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. 86649-57-2, name is 3-Pyridyloxyacetic acid, molecular formula is C7H7NO3, 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.

Add O-(7-azabenzotriazol- 1 -yl)-N,N,N?,N?-tetramethyluroniumhexafluorophosphate (584.56 mg, 1.81 mmol) and triethylamine (306.11 mg, 421.63 tL, 3.02 mmol) to a solution of 1-cyclopropyl-N-(1,2,3,4-tetrahydroisoquinolin-6-10 yl)methanesulfonamide (322.30 mg, 1.21 mmol) and 2-(3-pyridyloxy)acetic acid (185.30 mg, 1.21 mmol) in dimethylfomamide (6 mL). Stir the mixture at room temperature for 18 hours. Concentrate under reduced pressure. Pre-purify by an ion exchangechromatography, eluting with 10% methanol/dichloromethane followed by 2 N NH3 inmethanol. Concentrate the latter basic fraction and further purify the crude material by HPLC (XTeffa MS C18 21×100 m) eluting with a mobile phase of 20 mM ammonium carbonate at pH 9 in water/ACN (20% to 40% ACN over 8 minutes at 25 mL/minute) to afford the title compound (203 mg, 0.51 mmol). MS (m/z): 402 (M+1).

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 86649-57-2, 3-Pyridyloxyacetic acid.

Reference:
Patent; ELI LILLY AND COMPANY; BURKHOLDER, Timothy Paul; DEL PRADO, Miriam Filadelfa; FERNANDEZ, Maria Carmen; HEINZ II, Lawrence Joseph; PRIETO, Lourdes; ZHAO, Genshi; WO2015/54060; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6320-39-4 , The common heterocyclic compound, 6320-39-4, name is 3-Amino-4-hydroxypyridine, molecular formula is C5H6N2O, 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.

Step 1 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) piperidin-3-amine (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimeth yl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (100 mg, 0.24 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by the addition of 3-amino-4-hydroxypyridine (32.12 mg, 0.29 mmol) and potassium carbonate (67.19 mg, 0.49 mmol), then stirred at 60 C. overnight. After the reaction was completed, the reaction solution was diluted with water and then extracted with dichloromethane. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and separated by a preparative plate (Develop: EtOAc_MeOH=10:1) to give 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) piperidin-3-amine 339 (30 mg, yield: 28.01%). MS m/z (ESI): 441.2 [M+1] 1H NMR (400 MHz, CDCl3) 8.16 (s, 1H), 8.00 (s, 1H), 6.76 (s, 1H), 4.91 (s, 1H), 4.61-4.59 (m, 2H), 4.18 (s, 1H), 4.04-4.01 (m, 2H), 3.55-3.48 (m, 2H), 2.44 (d, J=12.0 Hz, 1H), 2.33-2.23 (m, 1H), 2.08-1.43 (m, 16H), 1.37 (s, 3H), 1.25-1.15 (m, 3H), 0.79 (s, 3H).

The synthetic route of 6320-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); 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. 1000340-35-1, name is 4-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, molecular formula is C8H5BrN2O, 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. SDS of cas: 1000340-35-1

Sodium borohydride (0.098 g, 0.0026 mole) was added in portions to a stirred suspension of 4-bromo-lH-pyrrolo [2, 3-b] pyridine-3-carboxaldehyde (0.4 g, 0.0017 mol) in methanol (15 inL) to obtain a clear solution. After completion of reaction, the reaction mixture was concentrated to obtain a residual mass that was diluted with water (25 mL) and extracted with ethyl acetate (25 mL x 3). The organic extracts were combined, dried over anhydrous Na2SC>4 and concentrated under vacuum to obtain the title compound. Yield: 0.35 g; – NMR (DMSO- , 400 MHz) delta ppm: 4.76 – 4.77 (d, J = 4.82 Hz, 2H), 4.86 -(bs, 1H), 7.28 – 7.29 (d, J = 5.04 Hz, 1H), 7.46 – 7.48 (d, J = 8 Hz, 1H), 8.02 – 8.03 (d, J = 5 Hz, 1H), 11.82 (s, 1H); Mass (m/z): 227.0 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 1000340-35-1.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (172 pag.)WO2018/42362; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 183208-35-7, 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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

[0653] To a stirred solution of 5-bromo-1H-pyrrolo [2, 3-bj pyridine (2 g, 10 mmol) in DMSO (20 mL) at room temperature under an argon atmosphere were added potassium hydroxide (852 mg, 15 mmol) and methyl iodide (1.95 mL, 30 mmol). The reaction mixture was warmed to room temperature and stirred for 4 h. After consumption of starting material (by TLC), the reaction mixture was diluted with ice cold water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filteredand concentrated in vacuo to obtain 5-bromo-1-methyl-1H-pyrrolo [2, 3-bj pyridine (2.1 g, crude) as colorless syrup used in the next step without further purification.LCMS: 98.9%; 212.7 (M+3); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 jtm); RT 2.49 mm; mobile phase: 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; T/B%:0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 30% EtOAc/ Hexane (R1: 0.6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1346575-64-1, 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. 1346575-64-1, name is 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

c) 6-(2-Dimethylamino-ethoxy)-l-isopropyl-lH-indole-4-carboxylic acid (6-methyl-2-oxo-4- propyl-1 , 2-dihydro-pyridin-3-ylmeth l)-amide To a cooled (0 C) mixture of 6-(2-dimethylamino-ethoxy)-l-isopropyl-lH-indole-4- carboxylic acid (400 mg, 1.37 mmol) in DMF (10 mL) was added EDC.HC1 (310 mg, 1.65 mmol) and HOBt.H20 (250 mg, 1.65 mmol). The reaction was stirred for 15 min, then DIPEA (1.2 mL, 6.89 mmol) and 3-aminomethyl-6-methyl-4-propyl-lH-pyridin-2-one (240 mg, 1.37 mmol) were added. The reaction was allowed to warm to RT and stirred for 16 h, at which time it was diluted with water (20 mL) and extracted with DCM (2×15 mL). The combined DCM layer was dried over Na2S04 and concentrated. The residue was purified by flash column chromatography eluting with 3% MeOH in chloroform and then further purified by preparative HPLC to furnish 6-(2-dimethylamino-ethoxy)-l-isopropyl-lH-indole-4- carboxylic acid (6-methyl-2-oxo-4-propyl-l,2-dihydro-pyridin-3-ylmethyl)-amide (120 mg, 19%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 0.92-0.88 (t, 3H), 1.43-1.41 (d, J = 6.8 Hz, 6H), 1.56 (m, 2H), 2.12 (s, 3H), 2.22 (s, 6H), 2.55-2.53 (m, 2H), 2.06 (m, 2H), 4.11-4.09 (t, 2H), 4.36-4.34 (d, J = 4.8 Hz, 2H), 4.76-4.73 (m, 1H), 5.90 (s, 1H), 6.74-6.73 (d, J = 2.8 Hz, 1H), 7.04 (s, 1H), 7.20 (s, 1H), 7.43-7.42 (d, J=3.2 Hz, 1H), 8.10-8.07 (bs, 1H), 11.55 (bs, 1H). LCMS (ES+): m/z= 453.23[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,1346575-64-1, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BRACKLEY, James; BURGESS, Joelle, Lorraine; GRANT, Seth; JOHNSON, Neil; KNIGHT, Steven, D.; LaFRANCE, Louis; MILLER, William, H.; NEWLANDER, Kenneth; ROMERIL, Stuart; ROUSE, Meagan, B.; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2011/140324; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 152460-10-1, 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 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The final target compounds were synthesized from 6-methyl-N-(4-(pyridin-3-yl) pyrimidin-2-yl) benzene-1,3-diamine 8(2 mmol), DMF (10 mL), and DIPEA (4 mmol) followed by substituted aromatic acid (2 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction mixture was poured into ice-cold water. The obtained yellow precipitate washed with water and dried to get target titled product pyrimidine scaffold benzamide derivatives (9 a-k).

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 152460-10-1, N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine.

Reference:
Article; Thirumurugan; Lakshmanan, Sivalingam; Govindaraj, Dharman; Daniel Prabu, D. Sam; Ramalakshmi; Arul Antony; Journal of Molecular Structure; vol. 1171; (2018); p. 541 – 550;,
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. 39890-95-4, name is 2-Chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H3ClF3N, 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. Application In Synthesis of 2-Chloro-6-(trifluoromethyl)pyridine

Step 1: Preparation of 6-trifluomethyl-pyridine-2-carboxylic acid methyl ester (2) To a solution of 2-chloro-6-trifluoromethyl-pyridine (2 g, 11.1 mmol, 1.0 eq) in MeOH (20 mL) was add Pd(OAc)2 (124 mg, 0.05 eq) and dppf (600 mg, 0.1 eq) under an atmosphere of nitrogen. Et3N (2.3 mL, 1.5 eq) was then added to the resulting orange solution. The reaction solution was then stirred under an atmosphere of carbon monoxide (40 psi) at 60 C. for 22 hr. Once the reaction completed, the mixture was filtered and the filtrate was concentrated in high vacuum. The residue was purified by column chromatography to afford the desired product. 1HNMR (400 MHz, CDCl3): delta 8.32 (d, J=8 Hz, 1H), 8.06 (t, J=8 Hz, 1H), 8.88 (d, J=8 Hz, 1H), 4.04 (s, 3H). LC-MS: m/z 206 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 39890-95-4.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC; Konteatis, Zenon D.; Popovici-Muller, Janeta; Travins, Jeremy; Zahler, Robert; Cai, Zhenwei; Zhou, Ding; US2015/18328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 886365-56-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 886365-56-6 as follows.

A mixture of 5-fluoro-3-methylpyridin-2-amine (3.3 g, 26.2 mmol) and dimethyl malonate(15.0 mL, 0.13 mol, 5.0 eq.) was heated at 210 C for 1.5 h. After cooling to room temperature,the precipitate was filtered and washed with ACN (3x) to give 7-fluoro-2-hydroxy-9-methyl- pyrido[1,2-a]pyrimidin-4-one as a dark solid (2.3 g), which was used directly in the next step. MS mlz 195.1 [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,886365-56-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GILLESPIE, Robert Jack; HASANE, Ratni; SARIE, Jerome Charles; (89 pag.)WO2016/184832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 215364-85-5, 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. 215364-85-5, name is 3-Bromo-2-chloropyridin-4-amine, molecular formula is C5H4BrClN2, 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 2 L 3 neck RBF was charged with 3-bromo-2-chloro-4-amino-pyridine (50.0 g, 241 mmol) in concentrated H2SO4 (36 mL) at 0 C. open to air. KNO3 (48.7 g, 482 mmol) was then added. The solution was allowed to first warm to room temperature (rt) for 1 h and then was heated to 90 C. for 3 h. The reaction mixture was cooled to rt and was poured into ice water. The obtained solids were filtered and washed with water. After drying under vacuum overnight 3-bromo-2-chloro-5-nitropyridin-4-amine was obtained as an orange-yellow solid (49 g, 81%). This was used directly without further purification.

According to the analysis of related databases, 215364-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Layek, Suman; Ji, Zhiqiang; Dyatkin, Alexey Borisovich; Boudreault, Pierre-Luc T.; Tsai, Jui-Yi; (251 pag.)US2019/393431; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem