Category: pyridine-derivatives

Reference of 119285-07-3 ,Some common heterocyclic compound, 119285-07-3, molecular formula is C14H22N4O2, 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.

(5-Bromo-2-chloro-pyrimidin-4-yl) -cyclopentyl-amine (0.155 g, 0.560 mmol) and 4- (5-amino-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (0.156 g9 0.560 mmol) were dissolved in toluene and heated to 115C for 48H. The reaction was cooled and concentrated. Purification on silica gel using 4: 1 HEXANE/ETOAC PROVIDED 0. 130 g (45%) OF 4- [5- (5-BROMO-4-CYCLOPENTYLAMINO- PYRIMIDIN-2-YLAMINO)-PYNIDIN-2-YL]-PIPERAZINE-1-CARBOXYLIC acid tert-butyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,119285-07-3, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/65378; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13534-99-1, 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. 13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, 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.

General procedure: To a solution of 2a, 2c or 2h (3 mmol, 0.5 g) in ethylene glycol (5 mL) was added successively the boronic acid (4.5 or 9.0 mmol, 1.5 or 3 equiv), Pd(PPh3)4 (1molpercent), and a solution of K3PO4 (6 mmol, 2 equiv) inwater (2 mL). The reaction mixture was heated at 80°C for 16 h and was then hydrolyzed with a 1 M solution of sodium hydroxide (20 mL). The aqueous phase was extracted with ethylacetate (3 x 30 mL) and the combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether/EtOAc (60/40) as eluent.

According to the analysis of related databases, 13534-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Silpa, Laurence; Niepceron, Alisson; Laurent, Fabrice; Brossier, Fabien; Penichon, Melanie; Enguehard-Gueiffier, Cecile; Abarbri, Mohamed; Silvestre, Anne; Petrignet, Julien; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 114 – 120;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 350-03-8, 1-(Pyridin-3-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, name: 1-(Pyridin-3-yl)ethanone, blongs to pyridine-derivatives compound. name: 1-(Pyridin-3-yl)ethanone

A mixture of 30 g of 3-acetylpyridine and 60 g of N, -dimethylformamidedimethylacetal was stirred for 6 hours under reflux with heat. After cooling down to room temperature, the mixture was concentrated under reduced pressure. 3-dimethylamino-l- (pyridin-3-yl ) – propenone (43 g) was obtained. 1 H-N R (CDC13) delta: 9.09-9.07 (1H, m) , 8.68-8.65 (1H, m) , 8.19 (1H, dt), 7.85 (1H, d) , 7.38-7.34 (1H, m) , 5.68 (1H, d) , 3.19 (3H, s), 2.96 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,350-03-8, 1-(Pyridin-3-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; ARIMORI, Sadayuki; SHUTO, Akira; MIZUNO, Hajime; WO2011/49150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 605-38-9, Adding some certain compound to certain chemical reactions, such as: 605-38-9, name is Dimethyl pyridine-2,3-dicarboxylate,molecular formula is C9H9NO4, 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 605-38-9.

Preparation of the starting substance: STR28 A solution of 19.5 g (0.1 mole) of 2,3-dimethoxycarbonyl-pyridine and 12 g (0.1 mole) of acetophenone in 300 ml of toluene is added dropwise to a suspension of 2.4 g (0.1 mole) of sodium hydride in 100 ml of toluene, while stirring. The mixture is then boiled under reflux for 3 hours, during which the methyl alcohol formed and about half of the toluene are distilled off. The residue which remains is poured onto a mixture of 15 g of ice and 7.2 g of acetic acid. The organic phase is separated off, the aqueous phase is extracted with chloroform (3 portions of 100 ml each) and the organic phases are combined, dried over sodium sulphate and evaporated in vacuo. The residue is fractionated over silica gel with chloroform as the mobile phase and chromatographed and the corresponding fractions are recrystallized from legroin. 17 g (60percent of theory) of 2-(1,3-dioxo-3-phenyl-prop-1-yl)-3-methoxycarbonyl-pyridine are obtained as white crystals of melting point 87° 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. 605-38-9, Dimethyl pyridine-2,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Aktiengesellschaft; US4752324; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6945-68-2, 5-Bromo-3-nitropyridin-2-amine, 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, COA of Formula: C5H4BrN3O2, blongs to pyridine-derivatives compound. COA of Formula: C5H4BrN3O2

2,3-Diamino-3-bromopyridine (40) A mixture of 2-amino-5- bromo-3-nitropyridine (676 mg, 3.10 mmol), Tin(II) chloride dihydrate (3.58 g, 14.0 mmol), and EtOH (3 mL) was heated to boiling. The resulting solution was refluxed under N2 for 15 h, cooled to room temperature, and evaporated to dryness. To the residual solid was added H2 O (80 mL) and basified to pH 8 with 1N aq NaOH. The resulting mixture was extracted with EtOAc (3*50 mL). The extracts were combined, washed with brine (25 mL), dried (K2 CO3), and rota-evaporated to dryness. The residual solid was dried at 40 C. under vacuum, giving 565 mg (97%) of 40 as a pale yellow powder, mp 158-160 C. 1 H NMR (CDCl3 +DMSO-d6) delta3.816 (s, 2H), 4.525 (s, 2H), 6,838 (s, 1H), 7.446 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6945-68-2, 5-Bromo-3-nitropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University and The University of Oregon, Eugene Oregon; The Regents of the University of California; ACEA Pharmaceuticals, Inc.; US5620978; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 889865-45-6, 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.889865-45-6, name is 2,3-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, molecular weight is 273.89, as common compound, the synthetic route is as follows.

To a solution of 2,3 -dichloro-4-iodopyri dine (50 g, 183 mmol, 1 equiv) in dioxane (500 mL) was added 2-ethylhexyl 3-sulfanylpropanoate (52 g, 237 mmol, 1.3 equiv), Xantphos (11 g, 18 mmol, 0.1 equiv), DIPEA (71 g, 547 mmol, 96 mL, 3 equiv) and Pd2(dba)3 (8.4 g, 9.1 mmol, 0.05 equiv). The reaction mixture was then warmed to 110 C and stirred for 2 hours. After this time, the reaction mixture was filtered and concentrated under reduced pressure. The crude residue so obtained was purified by silica gel chromatography to give 2-ethylhexyl 3 -((2,3- dichloropyridin-4-yl)thio)propanoate (42 g, 11 mmol, 63% yield) as a brown oil. 1H NMR (400 MHz, chloroform-d) delta 8.15 (d, J= 5.26 Hz, 1H), 7.02 (d, J= 5.26 Hz, 1H), 4.05 (d, J= 5.70 Hz, 2H), 3.25 (t, J= 7.45 Hz, 2H), 2.75 (t, J= 7.45 Hz, 2H), 1.62 – 1.53 (m, 1H), 1.42 – 1.26 (m, 8H), 0.88 (t, J= 7.45 Hz, 6H).

Statistics shows that 889865-45-6 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloro-4-iodopyridine.

Reference:
Patent; REVOLUTION MEDICINES, INC.; JOGALEKAR, Ash; WON, Walter; KOLTUN, Elena S.; GILL, Adrian; MELLEM, Kevin; AAY, Naing; BUCKL, Andreas; SEMKO, Christopher; KISS, Gert; (496 pag.)WO2018/13597; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 889865-45-6, 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. 889865-45-6, name is 2,3-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, 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.

Description 11; 3-Chloro-4-iodo-pyridin-2-ylamine (D11); A mixture of compound DlO (6 g, 21.9 mmol) in aqueous NH4OH (12 ml, 11 N) was heated at 129 0C for 12 h. After cooling to room temperature, DCM was added. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue thus obtained was purified by column chromatography (silica gel; DCM/MeOH(NH3) up to 2% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound DIl (2.88 g, 52%) as a white solid. LCMS: MW (theor): 254; [MH+]: 255; RT (min): 2.22. (Method 13)

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 889865-45-6, 2,3-Dichloro-4-iodopyridine.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; CID-NUNEZ, Jose, Maria; TRABANCO-SUAREZ, Andres, Avelino; MACDONALD, Gregor, James; WO2010/60589; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 101990-69-6, 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 101990-69-6 as follows.

EXAMPLE 7F 2 ,6-dichloroisonicotinaldehy de To a solution of EXAMPLE 7E (3.2 g, 18. 1 mmol) in dichloromethane ( 100 mL) was added Dess-Martin periodinane (9.2 g, 21.7 mmol) in portions and the mixture was stirred at room temperature for 30 minutes. The mixture was filtered and the filtrate was concentrated. The residue was purified by flash chromatography eluting with 1/20 ethyl acetate/ petroleum ether to afford the title compound. MS: 176 (M + HT).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,101990-69-6, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 624-28-2, Adding some certain compound to certain chemical reactions, such as: 624-28-2, name is 2,5-Dibromopyridine,molecular formula is C5H3Br2N, 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 624-28-2.

(S)-l-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-ol (Gl). A mixture of 2,5-dibromopyridine (12.2 g, 51.5 mmol) and (5)-hydroxypyrrolidine (2.80 g, 32.1 mmol) in toluene (50 mL) was heated to reflux overnight. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dissolved with EtOAc (150 mL), and the mixture was washed with aq. 10 % K2CO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane – > heptane/EtOAc 1 :2) yielded the title compound (3.62 g, 46%). LC-MS: tR = 0.48 min; ES+: 243.15.

According to the analysis of related databases, 624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 779345-37-8, 5-Fluoro-2-nitropyridine, 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, 779345-37-8, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Fluoro-2-nitropyridine

To a stirred solution of 5-fluoro-2-nitropyridine (1.00 g, 7.04 mmol) in ethanol (20 mL) was added hunig’s base (2.5 mL, 14.084 mmol) and 2-(3-fluorophenyl)pyrrolidine (1.74 g, 10.56 mmol) at room temperature. The resulting mixture was stirred at 100C for 16 h in a sealed tube. On completion, Reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with ethyl acetate (2 x 30 mL). Combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the title compound (1.8 g, 89%) as a pale brown solid. LCMS (ESI): m/z 288 [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,779345-37-8, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; MAANSSON, Kristoffer; HENRIKSSON, Krister; (76 pag.)WO2020/35557; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem