Category: pyridine-derivatives

Reference of 1227573-02-5 ,Some common heterocyclic compound, 1227573-02-5, molecular formula is C6H3BrFNO, 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 3: 2-Chloro-4-(5-fluoro-4-formyl-pyridin-3-yl)-benzonitrile (15c)To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (264 mg, 1.00 mmol), 3-bromo-5-fluoroisonicotinaldehyde (204 mg, 1.00 mmol) and PdCI2(PPh3)2 (56 mg, 0.08 mmol) in DMF (3 mL) was added 2M Na2C03 solution (1.50 ml, 3.00 mmol) under nitrogen atmosphere. The mixture was stirred and heated at 100C for 4hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4CI solution. After extraction and separation, the combined extracts were concentrated and purified by SNAPI Og (10%MeOH/DCM 0- 15%gradient) to give 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (47 mg, 18%) as a white solid.; ESI-MS m/z: 293 [M+MeOH+1]+, Retention time 1.15min. -NMR (CDCI3, 400 MHz) delta 7.33 (dd, J= 8.0, 1.6 Hz, 1 H), 7.50 (d, J= 1.6 Hz, 1 H), 7.78 (d, J= 8.0 Hz, 1 H), 8.49 (s, 1 H), 8.78 (d, J= 1.2 Hz, 1H), 10.27 (s, 1H)

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. 1227573-02-5, 3-Bromo-5-fluoroisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 685517-67-3, name is 2,6-Difluoro-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H2F2IN

n-Butyllithium (1.66mL, 4.15mmol, 2.5mol/L in hexane) was added dropwise to a solution of diisopropylamine (1.30mL, 4.15mmol) in THF (2mL) at -78C. After 25min 2,6-difluoro-3-iodopyridine (1.00g, 4.15mmol) in THF (5mL) was added dropwise into this mixture by cannula. After 12h at -78C, H2O (0.2mL, 11mmol) in THF (2mL) was added and the mixture was warmed to room temperature during 1h. The mixture was washed with 10% aqueous Na2SO3 (5mL) and extracted with ethyl acetate (3×50mL). The organic extracts were dried (MgSO4) and concentrated in vacuo. Crystallization from hexane afforded the product as colorless crystals (740mg, 74%). 1H NMR (400MHz, CDCl3): delta 7.22 (t, 2H,J=1.2). 13C NMR (100MHz, CDCl3): 161.1 (dd, J=250, 16, 2C), 115.6 (dd, J=24, 10, 2C), 110.3. 19F NMR (376MHz, CDCl3): delta -68.1. GC-MS m/z calcd. for C5H2F2IN [M+]: 241, found: 241. MP: 78-80C.

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, 685517-67-3, 2,6-Difluoro-3-iodopyridine.

Reference:
Article; Jin, Xin; Cramer, Jacob R.; Chen, Qi-Wei; Liang, Hai-Lin; Shang, Jian; Shao, Xiang; Chen, Wei; Xu, Guo-Qin; Gothelf, Kurt V.; Wu, Kai; Chinese Chemical Letters; vol. 28; 3; (2017); p. 525 – 530;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52311-50-9, Adding some certain compound to certain chemical reactions, such as: 52311-50-9, name is 2-Chloro-4-ethoxypyridine,molecular formula is C7H8ClNO, 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 52311-50-9.

Solid 2-chloro-4-ethoxypyridine (100 g 0.63 mol) was added to H2SO4(500 mL) slowly. Then 1-bromopyrrolidine-2 5-dione (124.2 g 0.70 mol) was added into above mixture at rt. The mixture was stirred at 80 for 3 h. TLC (PE/EA 101 Rf 0.5) showed the reaction was finished. The reaction mixture was poured into ice-water (2 L) and extracted with EA (1 L x 3) . The organic layer was washed with saturated Na2CO3solution (1 L x 2) dried over Na2SO4and concentrated. The residue was purified on silica column chromatography (PE/EA 601-301) . All fractions found to contain product by TLC (PE/EA 101 Rf 0.5) were combined and concentrated to yield 5-bromo-2-chloro-4-ethoxypyridine (60.9 g 0.26 mol 40yield) 1HNMR(400 MHz CD3OD) delta 8.31 (s 1H) 7.14 (s 1H) 4.32-4.10 (m 2H) 1.58-1.35 (m 3H) ES-LCMS m/z 237 (M+2)

According to the analysis of related databases, 52311-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885277-48-5, 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. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 2-bromo-6-methyl-3-pyridinecarboxylate D60 (1.15 g) and Pd(Ph3P)4 (0.2 g, 0.173 mmol) in 1,4-Dioxane (10 ml) stirred under nitrogen at room temperature tributyl(ethenyl)stannane (1.74 g, 5.50 mmol) was added neat in one charge. The reaction mixture was stirred at microwave Personal Chemistry at 95 C. for 30 minutes. The solvent was removed to give the crude title compound. Under similar conditions another batch of D60 (100 mg) was processed to give the crude title compound. The two crudes were joined and purified by flash chromatography on silica (80 g column, gradient elution from Cy to Cy/EtOAc 4:6) to afford the title compound D61 (1.0 g). UPLC (Basic GEN_C): rt=0.73 minutes, peak observed: 178 (M+1). C10H11NO2 requires 177. 1H NMR (400 MHz, CDCl3) delta ppm 8.08 (d, 1H), 7.66 (dd, 1H), 7.12 (d, 1H), 6.52 (d, 1H), 5.59 (dd, 1H), 3.93 (s, 3H), 2.63 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885277-48-5, Methyl 2-bromo-6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1254473-66-9, 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. 1254473-66-9, name is 1-(3,5-Dichloropyridin-4-yl)ethanol. A new synthetic method of this compound is introduced below.

A solution of 1- (3,5-dichloropyridin-4-yl) ethanol (II) (6 g, 31.24 mmol) in dichloromethane (DCM, 50 ml) was added portionwise over 10 min. PCC, 10.1 g, 46.86 mmol) at room temperature for 10 h.The insoluble matter was removed by filtration, and the residue was washed three times with DCM. The combined organic layers were concentrated to a crude product.Purification by silica gel column chromatography (petroleum ether: ethyl acetate = 20: 1) gave 5.10 g of colorless, turbid oil; Yield 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1254473-66-9, its application will become more common.

Reference:
Patent; Sichuan University; Wu, Yong; Hai, Li; Lei, Fan; Li, XiaoCen; (7 pag.)CN103819396; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 917364-11-5, Adding some certain compound to certain chemical reactions, such as: 917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid,molecular formula is C8H10N2O2, 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 917364-11-5.

Example 91N-((ls,4s)-4-(2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-4′-hydroxybiphenyl-3- yloxy)-5-fluoronicotinamido)cyclohexyl)-5,6,7,8-tetr ahydroimidazo [ 1 ,2-a] pyridine-2- carboxamide To a solution of 5,6,7, 8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (28.4 mg, 0.17 mmol) in acetonitrile (5 niL) was added DIPEA (0.057 niL, 0.34 mmol) and HATU (65.1 mg, 0.17 mmol). The mixture was allowed to stir at RT for 10 min before a solution of N-((ls,4s)- 4-aminocyclohexyl)-2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-4′-hydroxybiphenyl- 3-yloxy)-5-fluoronicotinamide (100 mg, 0.17 mmol) in acetonitrile (5 mL) with DIPEA (0.057 mL, 0.34 mmol) was added and the mixture stirred at RT for 30 mins. The reaction mixture was diluted in EtOAc (10 mL), washed with water, brine, dried (MgSO4) and evaporated to give a foam. This was purified by preparative HPLC to afford the title compound as a white solid. Yield: 31 mg1H NMR (400 MHz, CD3OD) delta 8.42 (d, J= 6.9 Hz, IH), 8.11 – 8.06 (m, 2H), 7.75 (s, IH), 7.57 – 7.42 (m, 4H), 7.38 (s, IH), 7.15 – 7.08 (m, IH), 6.92 (d, J= 8.5 Hz, IH), 4.16 – 4.07 (m, 5H), 3.98 – 3.89 (m, IH), 3.62 – 3.52 (m, 2H), 3.44 (d, J= 12.8 Hz, 2H), 2.95 (t, J= 6.2 Hz, 2H), 2.67 (t, J= 12.6 Hz, 2H), 2.10 – 1.64 (m, 12H), 1.32 (d, J= 6.7 Hz, 6H). MS: [M+H]+=696.4 (calc=696.3673) (MultiMode+)

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. 917364-11-5, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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.

To a stirred solution of diisopropyl amine (1.65 mL, 1 1.7 mmol) in anthydrous THF (10 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 4.80 mL, 12.0 mmol) slowly between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooled to 0C. The solution of LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (1.00 g, 5.8 mmol) in anhydrous THF( 20 mL ) at 0C. Upon complete addition of the LDA solution the resultant bright yellow suspension was stirred at 0C for 15 minutes. A solution of (3-fluoro-4- isothiocyanatophenyl)(methyl)sulfane (1.63 g, 8.2 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture and heated to 65C for 18 hours. The reaction mixture was cooled to room temperature and the volatiles removed in vacuo. The resultant brown gum was redissolved in THF, cooled to 0C and 10% aq acetic acid 10 mL added slowly. Acetonitrile (5 mL) was added slowly until a yellow solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound as a yellow solid (546mg, 20%). LC/MS: [M+l] 335. ‘HNMR ( 300 MHz, DMSO-d6): d 8.34 ( d, J=8.1 Hz, 1 H ), 7.85-8.20 ( m, 1H ), 7.61 ( t, J = 8.6 Hz, 1H ), 7.39-7.30 ( m, 2H ), 7.21 (d, J = 9.2 Hz, 1H ), 2.52 (s, 3H).

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; KINCAID, John; NEWSAM, John; KISAK, Edward; WOOTTON, Michael; KUSHWAHA, Avadhesh; (364 pag.)WO2020/106304; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166331-65-3, Adding some certain compound to certain chemical reactions, such as: 166331-65-3, name is 2-Chloro-6-isopropylnicotinic acid,molecular formula is C9H10ClNO2, 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 166331-65-3.

Preparation Example 10 2-Chloro-6-isopropylnicotinic acid (312 g), palladium carbon(10%) (16.0 g) and ethanol-water (6:1) (2000 mL) were stirred under a hydrogen atmosphere at room temperature for 3 days. The reaction solution was filtrated, and the filtrate was concentrated under reduced pressure. Ethyl acetate and a small amount of ethanol were added to the residue, and the precipitated solid was collected by filtration. The solid was added to cooled 1N-aqueous sodium hydroxide solution (1130 mL) and, after dissolution, the precipitated solid was collected by filtration. This was dissolved in chloroform, and dried over magnesium sulfate. The solvent was evaporated, the residual solid was suspended in hexane and collected by filtration to give 6-isopropylnicotinic acid (152 g) as white powder crystals. 1H-NMR(CDCl3)delta: 1.37(6H,d,J=6.9Hz), 3.29(1H,sept,J=6.9Hz), 7.38(1H,d,J=8.1Hz), 8.40(1H,dd,J=2.1,8.1Hz), 9.33(1H,d,J=2.1Hz).

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. 166331-65-3, 2-Chloro-6-isopropylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1852431; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89167-34-0, 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. 89167-34-0, name is 4-Chloro-3-iodopyridine. A new synthetic method of this compound is introduced below.

Step 1. 4-(2-fluoro-4-nitrophenoxy)-3-iodopyridine (52)[00376] To a stirred solution of 47 (346 mg, 1.445 mmol) in diphenyl ether (6 ml) was added sodium carbonate (459 mg, 4.34 mmol) and 2-fluoro-4-nitrophenol (681 mg, 4.34 mmol). The reaction mixture was heated to 17O0C for four hours then cooled-down to room temperature. The reaction mixture was diluted with dichloromethane, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (0% to 35% EtOAc in hexanes) to afford the title compound 52 (400 mg, 1.1 11 mmol, 77%) as a yellow solid. MS: 361.0 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89167-34-0, 4-Chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; METHYLGENE, INC.; RAEPPEL, Stephane; SAAVEDRA, Oscar; CLARIDGE, Stephen; VAISBURG, Arkadii; GAUDETTE, Frederic; ISAKOVIC, Ljubomir; DEZIEL, Robert; WO2008/46216; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 76041-79-7, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-ol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3BrF3NO

Step 1 : 5-Bromo-2-chloro-3-(trifluoromethv0pyridine (P46a)A solution of compound P45a (11.0 g, 45.8 mmol) in phenylphosphonicdichloride (22 mL) was heated at 140C overnight, cooled to rt, poured into ice water and extracted with EA. The organic layer was washed with sat. aq. NaHC03 and brine consecutively, dried over NaS04, filtered, concentrated and purified by CC (PE/EA = 5/1) to give compound P46a (10.5 g, 88%) as a yellow liquid.

The synthetic route of 76041-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem