Category: pyridine-derivatives

Electric Literature of 22245-83-6, 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 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 117 5-nitro-3-(trifluoromethyl)pyridin-2-ol; 2-Hydroxy-3-(trifluoromethyl)pyridine (3.0 g) was added to conc. sulfuric acid (18 mL) under ice-cooling, and the mixture was stirred at the same temperature for 5 min. Fuming nitric acid (90-95%, 7 mL) was added dropwise over 5 min, and the mixture was allowed to return to room temperature over 2 hr, heated to 50 C. and stirred for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice (200 g), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was washed with diisopropyl ether to give the title compound as a solid (yield 2.7 g, 69%). 1H-NMR (CDCl3) delta: 8.65-8.67 (1H, m), 8.80-8.81 (1H, m), 1H not detected.

According to the analysis of related databases, 22245-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1017789-38-6, name is tert-Butyl (4,6-dichloropyridin-2-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H12Cl2N2O2

1017789-38-6) (200 mg, 0.760 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (348 mg, 1.67 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.076 mmol), and potassium phosphate tribasic (484 mg, 2.28 mmol) in a flask was evacuated and backfilled with argon three times. Dioxane (3 mL) and water (0.33 mL) were added, and the reaction mixture was heated to 100C for 5 hours. The mixture was allowed to cool to room temperature. Hydrochloric acid (4.0 N in dioxane, 3.80 mL, 15 mmol) was added to the mixture, and the suspension was stirred vigorously for 14 hours at room temperature. The mixture was filtered and concentrated under reduced pressure. The residue was dissolved in DMSO and purified via reverse phase HPLC (15-50% acetonitrile/water with 0.1% TFA, linear gradient) to give 4,6-bis(l -methyl- lH-pyrazol-4-yl)pyridin-2-amine. MS ESI calc’d. for C13H15N6 [M + H]+ 255, found 255. 1H NMR (500 MHz, DMSO-d6) delta 8.46 (s, 1H), 8.42 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70-7.59 (m, 2H), 7.40 (s, 1H), 6.80 (s, 1H), 3.93 (s, 3H), 3.90 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1017789-38-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DONOFRIO, Anthony; ELLIS, John Michael; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; WO2013/52393; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.10177-29-4, name is 4-Chloronicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.5545, as common compound, the synthetic route is as follows.Recommanded Product: 4-Chloronicotinic acid

A mixture of amine 4 (1eq.), carboxylic acid (1.2 eq.), diisopropylethylamine (DIEA) (1.5 eq.), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimidehydrogen chloride (EDC·HCl) (1.2 eq.) in dichloromethane was stirred at room temperature for18 h. The reaction mixture was diluted with dichloromethane and washed withwater and brine. The organic layer was dried over MgSO4 andconcentrated. The crude product was purified by normal phase column chromatography(SP1, Biotage) to yield compound 5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10177-29-4, 4-Chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Article; Hwang, Jong Yeon; Smithson, David C.; Holbrook, Gloria; Zhu, Fangyi; Connelly, Michele C.; Kaiser, Marcel; Brun, Reto; Kiplin Guy; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4127 – 4131;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1060812-84-1 ,Some common heterocyclic compound, 1060812-84-1, molecular formula is C7H5BrN2, 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.

A solution mixture of 5-bromopyrazolo[1 ,5-a]pyridine 94-2 (900 mg, 4.59 mmol) and tBuONa (661 .2 mg, 6.88 mmol) in toluene (10 mL) was degassed with argon for about 10 mm. To this mixture were added Pd2(dba)3 (84 mg, 0.091 mmol), BINAP (114.2 mg, 0.lO2mmol) and cyclopropylamine (2 mL, 28.87 mmol) under argon atmosphere. The resulting reaction mixture was maintained at 90C for 2 h under microwave irradiation. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was washed with water (30 mL), brine (25 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography over silica-gel (100-200 mesh) using a solvent gradient of 25% ethyl acetate in pet-ether to afford 500 mg (62%) of N-cyclopropylpyrazolo[1,5-a]pyridin-5- amine 147-1 as a brown solid. 1H-NMR (400 MHz, CDCI3): c58.18 (d, J= 7.5 Hz, 1H), 7.78 (d, J= 2.2 Hz, 1H), 6.72 (d, J= 2.6 Hz, 1H), 6.15-6.18 (m, 2H), 4.28 (5, 1H), 2.44-2.49 (m, 1 H), 0.78-0.80 (m, 2H), 0.54-0.58 (m, 1 H). ESI-LC/MS: m/z 173.75 (M+H); R =1 .99 mm [Waters Acquity UPLC with Quattro-micro detector; Waters Acquity BEH Cl 8,1.7 pm, 2.1 X 50 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) hold for 0.5 mm and to 10:90 H20 (0.025% TEA):CH3CN (0.025% TEA) in 3.5 mm and hold for 1 .5 mm with flow rate of 0.4 mLlmin].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060812-84-1, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99163-12-9 ,Some common heterocyclic compound, 99163-12-9, molecular formula is C12H9NO, 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: Respective aromatic/hetro aromatic aldehydes (6a-r) (0.43 mmol) was added to a pre-mixed solution of compound 5 (0.43 mmol) in ethanol. The reaction content was refluxed for 0.5 h. The solids was filtered and rinsed with ethanol and dried to afford the respective hydrazone derivatives (7a-r) in 82-93 % yield (Scheme-I).

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. 99163-12-9, 4-Pyridin-4-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sree Lakshmana Rao; Basaveswara Rao, Mandava V.; Prasad; Asian Journal of Chemistry; vol. 31; 3; (2019); p. 627 – 632;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 106651-81-4 ,Some common heterocyclic compound, 106651-81-4, molecular formula is C7H9Cl2N, 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-(2-Methoxycarbonylethyl)adenine (313 mg, 1.51 mmol) obtained by Reference example 22 and potassium carbonate (0.44 g, 3.18 mmol) were added to DMF (40 ml). The mixture was at 70C for 1 hour and then cooled to room temperature. Thereto was added 6-methyl-3-pyridylmethyl chloride hydrochloride (0.38 g, 2.13 mmol) and the mixture was stirred at room temperature for 15 hours. After removing the solvent, the residue was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (SiO2 20g, eluting solvent: CHCl3/MeOH = 100/1 ~ 30/ 1) to give the captioned compound (358 mg, 1.15 mmol) as a white solid.

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. 106651-81-4, 5-(Chloromethyl)-2-methylpyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1550662; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103-74-2, 2-(2-Hydroxyethyl)pyridine, 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, HPLC of Formula: C7H9NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9NO

General procedure: To a solution of A1B1 (1.0mmol) and triphenylphosphine (1.5mmol) in anhydrous tetrahydrofuran (3mL), added C1 or C2 (2.0mmol) and dropwise added diethyl azodicarboxylate (DEAD, 1.5mmol) in anhydrous and anoxybiotic conditions. The reaction mixture was stirred at-2C for 30min, and then stirred at room temperature for 24h. After completion of reaction was monitored through TLC, the reaction mixture was filtered and washed with ether and saturated salt water to get products because there would be a solid precipitate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103-74-2, 2-(2-Hydroxyethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Article; Wang, Fang; Sun, Jun-Rong; Huang, Mei-Yan; Wang, Hui-Ying; Sun, Ping-Hua; Lin, Jing; Chen, Wei-Min; European Journal of Medicinal Chemistry; vol. 72; (2014); p. 35 – 45;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, 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, Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, blongs to pyridine-derivatives compound. Safety of 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

[Referential Example 13] Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxylate: 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (531 mg) was dissolved in absolute diethyl ether (20 ml), n-butyllithium (1.54N hexane solution, 1.63 ml) was added dropwise at -78C, and the mixture was stirred for 30 minutes with ice cooling. After passing carbon dioxide into the reaction mixture at -78C for 1 hour, the mixture was warmed to room temperature. The reaction mixture was concentrated under reduced pressure to obtain the title compound (523 mg) as a pale brown solid. 1H-NMR (DMSO-d6) delta: 2.37(3H,s), 2.64-2.77(4H,m), 3.54(2H,s) MS (FAB) m/z: 199(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,143150-92-9, 2-Bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1270557; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 174669-74-0, name is 2-Fluoropyridin-3-ol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H4FNO

Iodomethane 1.7 mL (27 mmol) and cesium carbonate 4.3 g (13. mmol) were added to a DMSO (20 mL) solution of 2-fluoropyridin-3-ol 1.0 g (8.8 mmol), and the mixture was stirred at 60C for 1 hour. After the completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound 1.1 g (8.7 mmol, yield 99%) as a white solid. 1H-NMR spectrum (400MHz, DMSO-d6) delta:7.76 – 7.69 (m, 1H), 7.65 (ddd, J = 1.5, 8.0, 10.7 Hz, 1H), 7.31 (ddd, J = 0.9, 4.8, 8.0 Hz, 1H), 3.88 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 174669-74-0.

Reference:
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol, 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, Formula: C8H8ClNO, blongs to pyridine-derivatives compound. Formula: C8H8ClNO

A mixture of intermediate 4 (0.0003 mol) and 4-chloro-6,7-dihydro- 5H- cyclopenta[b]pyridin-7-ol (0.0003 mol) was stirred at 1500C for 20 minutes, cooled to room temperature, extracted with NaHCOs/DCM/methanol (few drops). The organic layers were combined, dried over MgSO4, filtered off and the solvent was evaporated. The residue (0.174g) was purified by column chromatography over silica gel (DCM/methanol 95/5, 93/7 to 90/1 ). The pure fraction was collected and the solvent was evaporated, yielding 0.097 g (68%) of compound 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/37343; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem