Category: pyridine-derivatives

Application of 185315-53-1 ,Some common heterocyclic compound, 185315-53-1, molecular formula is C6H5Cl2N, 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: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 34; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin- 1 -yl) -3 – [ [2- (trifluoromethyl)phenyl] methyl] triazolo [4, 5 -d] pyrimidin- 5 – amine (example 22) the title compound was prepared from (3S)-3-methyl-l-(5- morpholino-3H-triazolo[4,5-d]pyrimidin-7-yl)pyrrolidin-3-ol and 3-chloro-2- (chloromethyl)pyridine. MS(m/e): 431.3 (MH+).

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. 185315-53-1, 3-Chloro-2-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6515-09-9, 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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To fuming HNO3 (136 rn) were added H2S04 (111 rn) and 23,6-trichoropyridine (24.2g, 133 mmo) at 0C. The reaction mixture was sHowed to warm to RT, then stirred at100C overnight. After cooing to 0C, the mixture was poured onto ice-water. Theunsoube materia was coHected by fitration to afford 2,3,6-trichoro-5-nitropyridine. Rt =1.07 mm (UPLC Method B2), 1H NMR (400 MHz, DMSO-d6) 6 ppm: 9.06 (s, 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 6515-09-9, 2,3,6-Trichloropyridine.

Reference:
Patent; NOVARTIS AG; PISSOT SOLDERMANN, Carole; QUANCARD, Jean; SCHLAPBACH, Achim; SIMIC, Oliver; TINTELNOT-BLOMLEY, Marina; ZOLLER, Thomas; (161 pag.)WO2015/181747; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 120739-77-7 ,Some common heterocyclic compound, 120739-77-7, molecular formula is C8H11ClN2, 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.

(2) 20.16 g of the above crude product were dissolved in 114 ml of chloroform and to the resulting solution was added a solution of 26.34 g (0.2486 mol) of sodium carbonate in 114 ml of water at 2-7 C. with stirring. Then, 13.5 g (0.0791 mol) of N-(6-chloro-3-pyridyl)methyl-N-ethylamine were dropwise added to the mixture at 5-6 C. and stirred for 40 minutes. Further, 31.59 g (0.407 mol) of 40% methylamine were dropwise added to the mixture at 3-7 C., followed by stirring for 30 minutes under ice-cooling and 30 minutes at room temperature. The separated aqueous layer was extracted with 48 ml of chloroform. The combined chloroform layers were concentrated, and the residue to which 39 ml of ethyl acetate were added was ice-cooled to precipitate pale yellowish crystals of 1-[N-(6-chloro-3-pyridyl)methyl-N-ethyl]amino-1-methylamino-2-nitroethylene. Yield: 18.15 g (84.9%). mp. 83-84 C.

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. 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5364989; (1994); A;,
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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine

Procedure for synthesis of N-[6-chloro-4-(trifluoromethyl)-3-pyridyl]-2,2-dimethyl- propanamide (Step 1) A mixture of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (commercially available) (75 mg, 0.288 mmol), 2,2-dimethylpropanamide (32 mg, 0.317 mmol), XantPhos Pd G3 precatalyst (13 mg, – – 0.014 mmol), K2C03 (79 mg, 0.57 mmol) in 1 ,4-Dioxane (0.5 ml.) was heated at 90C for 0.5h and then 1 10C for 2h. Purification by reverse phase HPLC delivered product (14 mg, 15%). LC-MS: (positive ES MH+ 281 ).

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PHADTE, Mangala; SONAWANE, Ravindra; MORRIS, James Alan; BOEHMER, Jutta Elisabeth; DESSON, Timothy Robert; RUSSELL, Sally Elizabeth; LING, Kenneth; HENNESSY, Alan Joseph; HOTSON, Matthew Brian; LONGSTAFF, Adrian; RUSSELL, Claire Janet; GOODWIN-TINDALL, Jake; WO2015/52076; (2015); 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, molecular formula is C7H6N2O4, 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-Methyl-5-nitro-3-pyridinecarboxylic acid

A solution of 2-methyl-5-nitronicotinic acid 1 (50 mg, 0.27 mmol), intermediate II (90 mg, 0.41 mmol), PyBOP (281 mg, 0.54 mmol) and DIEA (0.14 ml, 0.81 mmol) in DCM/DMF (6 ml, 5:1) was stirred at 20C for 16 hr. The mixture was washed with saturated aq. NaHCO3, H2O, dried over MgSO4, and evaporated, and the residue was chromatographed on reverse phase HPLC (10-95% AcN in H2O) to give 3 (92 mg) as a brown solid. (Calculated mass: 365.4, observed mass: 364.6).

With the rapid development of chemical substances, we look forward to future research findings about 59290-81-2.

Reference:
Patent; KEMIA, INC.; WO2007/56016; (2007); A2;,
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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, the common compound, a new synthetic route is introduced below. Application In Synthesis of N-((6-Chloropyridin-3-yl)methyl)ethanamine

To prepare compound 4e a solution of 4d (1 mmol) and N-((6-chloropyridin-3-yl)methyl)ethanamine (0.187 g, 1.1 mmol) in acetonitrile (4 mL) was heated under reflux. The progress of the reaction was monitored by TLC. After completion, the cooled mixture was filtered and the precipitate was washed with cold acetonitrile (4 mL) to afford the desired product 4e.

The synthetic route of 120739-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Nanyang; Xia, Shanshan; Zou, Minming; Shao, Xusheng; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5293 – 5300;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1190862-70-4, Adding some certain compound to certain chemical reactions, such as: 1190862-70-4, name is Ethyl 5-bromo-6-methylnicotinate,molecular formula is C9H10BrNO2, 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 1190862-70-4.

17C: A mixture of 1A (250 mg, 0.605 mmol), bis(pinacolato)diboron (192 mg,0.756 mmol), potassium acetate (178 mg, 1.815 mmol) and PdC12(dppf)-CH2C12 adduct (24.70 mg, 0.030 mmol) in dioxane (6 mL) was heated at 100 C for 60 mm. After cooling to rt, ethyl 5-bromo-6-methylnicotinate (150 mg, 0.615 mmol) and1,1 ?-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (20.03 mg, 0.031 mmol) were added. The reaction mixture was degassed by nitrogen sparge for 5 mm. 2M K3P04 (aq) (0.922 mL, 1.844 mmol) was quickly added and the reaction mixture heated at 100 C for 15 mm. After cooling to rt, volatiles were removed in vacuo. The cmde residue was purified with column chromatography on the Isco system (40 g, 0-100%EtOAc/Hex to afford 17C (300 mg, 0.573 mmol, 93 % yield) as a crystalline beige solid. MS ESI m/z 498.0 (M+H)

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. 1190862-70-4, Ethyl 5-bromo-6-methylnicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUO, Junqing; HART, Amy, C.; MACOR, John, E.; MERTZMAN, Michael, E.; PITTS, William, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; CHEN, Jie; DZIERBA, Carolyn, Diane; LUO, Guanglin; SHI, Jianliang; SIT, Sing-Yuen; (428 pag.)WO2018/148626; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 562825-95-0, 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 562825-95-0 as follows.

A mixture consisting of ethyl (3-nitropyridin-4-yl) amine (11.76 g, 70 mmol) in acetic acid (140 ml) with sodium acetate (28.7 g, 350 mmol) and bromine (13.44 g, 84 mmol) was stirred in a sealed flask at 100 oc for 18 h. Most of the solvent was removed in vacuo and the residue partitioned between CH2CI2 and water and the aqueous layer basified with NaHCO3. The organic extract was washed with water then brine, dried (Na2SO4) and all volatiles removed in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate: hexane (2: 8) to afford the title compound (10.4 g, 60%). MS: (M+H) + = m/z 246.; A mixture of ethyl (3-nitropyridin-4-yl) amine (11.8 g, 70.0 mmol), acetic acid (140 mL), sodium acetate (28.7 g, 0.35 mol) and bromine (13.4 g, 84.0 mmol) was stirred in a pressure vessel at 100 C for 18 h. The solvent was removed in vacuo and the residue partitioned between CH2CI2 and water. The aqueous layer was made basic (pH No. 8) with NaHCO3 and further extracted with CH2CI2. The combined organic extracts were washed with water, brine and dried (Na2SO4). The solvent was removed in vacuo. and the residue subjected to flash chromatography (20% EtOAc/hexanes, silica gel) to give 10.4 g (60%) of the desired compound. MS (ES+) m/z 246 (M+H) +.; To a solution of the product of 14 (a) (3. 0g, 17. 9mmol) in acetic acid (40ml) was added bromine (3.12g, 1ml, 19. 7mmol) and the mixture was heated at 100C for 20 hours. After cooling the solvent was removed in vacuo and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase was washed with water (x3), dried and evaporated in vacuo. Purification of the residue by silica gel chromatography eluting with 50% dichloromethane in ethyl acetate afforded the title compound (1.9g, 43%).’H NMR (DMSO-d6) 8.73 (1H, s), 8.52 (1H, s), 7.0 (1H, br), 3.25 (2H, m), 1.16 (3H, t, J 7.2Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,562825-95-0, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 696-42-4, 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.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.

To a stirred solution of 5-fluoropyridine-3-carbonitrile (2.0 g, 16.38 mmol) in methanol (20 mL) at RT was added NaOMe (88mg, 1.64 mmol) and the reaction stirred at RT overnight. Ammonium chloride (1 .40g, 26.21 mmol) was added in a single portion and the reaction mixture stirred overnight at RT. The reaction mixture was filtered and the filtrate concentrated to dryness under reduced pressure. The residue was suspended in EtOH (50 ml_) and then heated at reflux. The undissolved solid was filtered off and the filtrate concentrated to 1/3 of its volume and then left to stand at RT. The resultant crystals were filtered off, washed with EtOH and air-dried to give the desired product (2.1 1 g, 73%) as white crystals. 1H NMR (400 MHz, d6-DMSO) delta 8.93 (d, 1 H), 8.88 (s, 1 H), 8.29-8.23 (m, 1 H).

The chemical industry reduces the impact on the environment during synthesis 696-42-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; BRIGGS, Emma; CARTER, Neil, Brian; MORRIS, Melloney; TATE, Joseph, Andrew; (55 pag.)WO2019/57720; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 90145-48-5, 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. 90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, 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.

Example 5 Preparation of 5-bromo-N-(1-(4-chlorophenylamino)-2-(naphthalen-1-yl)-2- oxoethvDpicolinamide (Compound-1) [0095] A mixture of 5-bronnopicolinannide 111 (0.588 g, 2.92 mmol) and 2,2- dihydroxy-1 -(naphthalen-1 -yl)ethanone 112 (1.20 g, 5.67 mmol) in dioxane (20 ml_) were heated at 100 0C for 18 hours. The dioxane was removed under vacuum and the residue was dissolved in chloroform and methanol and concentrated onto silica gel. The material was purified by auto flash system (CH2CI2 to 1 % MeOH: CH2CI2) to give 5- bromo-N-(1-hydroxy-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide 113 as a tan solid (0.74 g, 66%). [0096] 5-bromo-N-(1 -hydroxy-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide 113(0.74 g, 1.93 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.43 g, 1.96 mmol). The mixture was heated to 50 0C for 30 minutes and cooled to 0 0C. 4-Chloroaniline 114 (0.512 g, 4.01 mmol) in THF (10 ml_) was added and allowed to react for 1 hour. The reaction was quenched with water and the product was extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and concentrated onto silica gel. The product was purified by auto flash column chromatography (30 to 50% CH2CI2: hexane) followed by titration with diethyl ether to give 5-bromo-N-(1-(4- chlorophenylamino)-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide (Compound-1 , 352 mg, 37%). 1H NMR (300 MHz, CDCI3): delta = 8.83 (d, J = 8.7 Hz, 1 H), 8.50 (d, J = 1.5 Hz, 1 H), 8.46 (d, J = 9.6 Hz, 1 H), 8.39 (dd, J = 1.2, 7.2 Hz, 1 H), 8.07-8.03 (m, 2H), 7.93 (dd, J = 2.4, 8.7 Hz, 1 H), 7.89 (d, J = 7.5 Hz, 1 H), 7.68-7.63 (m, 1 H), 7.56 (t, J = 7.8 Hz, 2H), 7.16 (d, J = 8.7 Hz, 2H), 7.09-7.03 (m, 1 H), 6.82 (d, J = 9.0 Hz, 2H) 5.41 (d, J = 8.1 Hz, 1 H).

According to the analysis of related databases, 90145-48-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem