Month: March 2022

Electric Literature of 402-65-3, 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. 402-65-3, name is 2-Fluoroisonicotinic acid, molecular formula is C6H4FNO2, 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.

Intermediate 1; 3-[(2-Wi/oro-4-iodophenyl)amino]isonicotinic acid (R = Fluoro); A mixture of 2-fluoro-4-iodoaniline (20.0 g, 84.38 mmol) in dry THF (80 mL) was cooled to – 67 0C (dry ice/IPA bath) under nitrogen, prior to” slow addition of 1.0 M lithium bis(trimethylsilyl)amide (255 mL, 255 mmol) via addition funnel, at a rate that kept the internal temp below -59 0C (~2 h). After final addition, the yellow-green slurry was stirred for 30 min and then treated with 2-fluoroisonicotinic acid (8.0 g, 56.69 mmol). The bath was not removed, but the contents were allowed to slowly warm to room temp. After 4 days, the dark slurry was poured into a biphasic mixture of aqueous 2.0 lf sodium hydroxide (1000 mL) and ethyl acetate (150 mL). The aqueous layer was separated and the organics were again extracted with base (1000 mL). The pH of the two aqueous layers was adjusted to ~2 with concentrated hydrochloric acid. A yellow solid precipitated, which was filtered. The resultant yellow cake was washed with water (2 x 400 mL) and dried under high vacuum at 40 0C (17- 19 g). LC/MS [(5.2 min; 359 (M+1)].

According to the analysis of related databases, 402-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/45514; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62135-58-4 ,Some common heterocyclic compound, 62135-58-4, molecular formula is C9H9N3O2, 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.

To a stirred solution of ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (2.4 g, 12.55 mmol) in MeOH (20 mL) and THF (10 mL) was added NaBH4 (950 mg, 25.1 mmol) portionwise at 0 C. The mixture was stirred at RT for 2 h. The reaction mixture was quenched with saturated aqueous NH4Cl and concentrated in vacuo. The residue was dissolved in DCM/MeOH (100 mL), filtered, and the filter cake was rinsed with DCM/MeOH (50 mL). The combined filtrate was concentrated and purified by silica gel chromatography (EA/PE=1/1) to give [1,2,4]triazolo[1,5-a]pyridin-2-ylmethanol (1.6 g, yield: 85%) as a yellow solid. ESI-MS [M+H]+: 150.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62135-58-4, its application will become more common.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, 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, Recommanded Product: 5-Bromo-2-methoxyisonicotinaldehyde, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-2-methoxyisonicotinaldehyde

To a solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (23.5 g, 108.8 mmol) in MeOH (100 mL) were successively added a solution of I2 (35.9 mg, 141.4 mmol) in MeOH (75 mL) and a solution of KOH (15.9 g, 282.8 mmol) in MeOH (75 mL) at 0 C. The resulting mixture was stirred for 1 hr at 0 C and the reaction was quenched with saturated aqueous NaHS03. The resulting mixture was diluted with DCM (400 mL). The separated organic phase was washed with H20 (150 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column (eluting with PE_EA=20: 1, v:v) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (14.9 g) as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 188637-63-0 ,Some common heterocyclic compound, 188637-63-0, molecular formula is C6H7BrN2, 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.

To a solution of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (582mg, 1.61 mmol) and 6-bromo-pyridin-2yl-methylamine (300mg, 1.61 mmol) in DMF was added CDI (261 mg, 1.61 mmol). The reaction mixture was stirred at r.t. for 2 h. The reaction mixture was purified on RP-HPLC to give N-((6-bromopyridin-2-yl)methyl)-6-(2- cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide (700mg, 82%) LRMS (M+H+) m/z 530.1.

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. 188637-63-0, (6-Bromopyridin-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYTOKINETICS, INCORPORATED; WO2008/16643; (2008); A2;,
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 824-52-2, name is 5-Methyl-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Methyl-1H-pyrrolo[2,3-b]pyridine

Compound 3 (0.50 g, 3.8 mmol), methenamine (0.8 g, 5.7 mmol) was added to a three-necked flask,Water (5 mL) and acetic acid (2.5 mL);The reaction was heated to reflux for 4 hours. The reaction was cooled to room temperature and extracted with ethyl acetate (30 mL x 3); the organic phases were combined and washed with saturated brine (30 mL)Dry over sodium sulfate and filter. The filtrate was spin-dried, and the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 1: 2 by volume)A pale yellow solid was obtained, compound 4 (0.3 g, 1.9 mmol, 49%)

With the rapid development of chemical substances, we look forward to future research findings about 824-52-2.

Reference:
Patent; Kanghua (Shanghai) Drug Discovery Co., Ltd.; Ma Jingxiang; (5 pag.)CN107056781; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89809-65-4 ,Some common heterocyclic compound, 89809-65-4, molecular formula is C8H6N2O2, 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.

6-Cyanonicotinic acid methyl ester (701 mg) was dissolved in a mixed solvent of methanol (1 ml) and tetrahydrofuran (7 ml) and sodium borohydride (197 mg) was added under icecooling. The mixture was directly heated to room temperature and stirred overnight. Water (20 ml) was added, and the mixture was extracted with ethyl acetate (once with 50 ml and once with 30 ml), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified with column chromatography (Yamazen HI-FLASH COLUMN size 2L, elution solvent: hexane/ethyl acetate) to give the title compound (264 mg). 1H-NMR(CDCl3)delta:2.09(1H,m), 4.86(2H,d,J=5.1 Hz), 7.71(1H,d,J=8.1 Hz), 7.89(1H,dd,J=1.8 Hz,8.1 Hz), 8.70(1H,s). MS:135(M++1).

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. 89809-65-4, Methyl 6-Cyanopyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2154135; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 131747-53-0, 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. 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol, molecular formula is C7H6F3NO, 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-Chloro-4-((6-(trifluoromethyl)pyridin-2-yl)methoxy)pyridine 6-(Trifluoromethyl)-2-pyridinemethanol (2.20 g, 12.8 mmol) was reacted according to Example 113 (step c) to provide the title compound (3.30 g, 89%) as a white foam: ESI MS m/z 289 [M+H]+.

According to the analysis of related databases, 131747-53-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Albany Molecular Research, Inc.; SURMAN, Matthew D.; FREEMAN, Emily E.; GUZZO, Peter R.; HENDERSON, Alan J.; HADDEN, Mark; US2014/163012; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1151989-04-6, 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. 1151989-04-6, name is 4-Nitrophenyl 4-(pyridin-2-yldisulfanyl)benzyl carbonate. A new synthetic method of this compound is introduced below.

Synthesis of Compound 9:Doxorubicin hydrochloride in the dark at room temperature (DOX·HCl, 127 mg, 0.22 mmol, 1 eq)Dissolved into dry dimethylformamide (4 mL),Triethylamine (34 mg, 46 muL, 0.33 mmol, 1.5 eq) was added slowly.The reaction solution was stirred at room temperature for 0.5 hour.Compound 8 (95 mg, 0.23 mmol, 1.05 eq) was added slowly,A solution of traces of 4-dimethylaminopyridine in dimethylformamide (2 mL).The reaction was carried out in the dark at room temperature and poured directly into water. The precipitated solid was filtered, washed with purified water and dried under vacuum.The crude product was further purified by rapid preparative column chromatography (methanol: dichloromethane, 1:50 to 1:10 v/v)Obtained as a dark red solid (61 mg, 34%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1151989-04-6, its application will become more common.

Reference:
Patent; Fudan University; Sun Tao; Jiang Chen; (22 pag.)CN109846824; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 87674-15-5, Adding some certain compound to certain chemical reactions, such as: 87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol,molecular formula is C7H8FNO, 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 87674-15-5.

A mixture of 1-(3-fluoropyridin-4-yl)ethanol (10 g, 70.3 mmol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-fluoro-4-acetyl pyridine (6.9 g, 70%) that was used directly in the next step.

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. 87674-15-5, 1-(3-Fluoropyridin-4-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142414; (2007); 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. 490-11-9, name is Pyridine-3,4-dicarboxylicacid, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5NO4

To a solution of pyridine-3,4-dicarboxylic acid (7.00 g, 41.9 mmol) and4-dimethylaminopyridine (80 mg, 0.65 mmol) in methanol (230 mL) was added thionylchloride (24.9 g, 210 mmol) at 0 C. The mixture was stirred at 0 C for 30 minutes.Reaction temperature was then raised up to reflux with constant stirring overnight.Having cooled down to room temperature, the reaction mixture was concentrated under reduced pressure to give a residue, which was re-dissolved in water (200 mL). The prepared solution was adjusted to pH 89 with saturated sodium bicarbonate aqueous solution at 0C. Then the aqueous was extracted with ethyl acetate (150 mL) for three times. The combined organic layers were washed with brine (200 mL), dried over Na2 SO4() and filtered. The filtrate was concentrated under reduced pressure to give the title compound (5.26 g, 64 % yield) as yellow oil. LC-MS (ESI): RT = 1.27 mm, mass calcd. for C9H9N04 195.1, mlz found 196.4 [M+H]. ?H NIVIR (400 1VIHz, DMSO-d6)9.02 (d, J 0.8 Hz, 1H), 8.91 (d, J 5.2 Hz, 1H), 7.70 (d, J= 5.2, 0.8 Hz, 1H), 3.87 (s,6H).

The synthetic route of 490-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; WAN, Zhao-Kui; JIANG, Yimin; DAI, Xuedong; LIU, Qian; CHEUNG, Wing Shun; DENG, Gang; FU, Liqiang; (547 pag.)WO2019/1420; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem