Tag: M.W:200-300

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 886365-28-2, name is Methyl 5-bromo-2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 886365-28-2

Methyl 5-bromo-2-chloro isonicotinate (30 g, 120 mmol) was dissolved in 1,4-dioxane (300 mL), and 3,5-dimethoxyphenylacetylene (20.4 g, 120 mmol), CuI (2.28 g, 12 mmol), Pd(dppf)Cl2 (4.2 g, 6 mmol) and Et3N (12.0 g, 120 mmol) were added, and the mixture was heated to 60 C. under N2, for 6 h. The reaction was complete, and the mixture was filtered and concentrated. The crude product was separated by silica gel column chromatography (DCM:PE=20:1) to obtain compound methyl 2-chloro-5-((3,5-dimethoxyphenyl)ethynyl)isonicotinate (22 g, yield: 55%). MS (ESI): m/z 332.1 [M+1]+.

With the rapid development of chemical substances, we look forward to future research findings about 886365-28-2.

Reference:
Patent; Abbisko Therapeutics Co., Ltd.; YANG, Fei; DENG, Haibing; YING, Haiyan; YU, Hongping; CHEN, Zhui; XU, Yaochang; (604 pag.)US2019/270742; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72587-15-6, 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 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Production Method of 2-Methyl-1-phenylpropan-2-yl 3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate Sodium hydride (240 mg, 3 Eq) was dissolved in DMA (dimethylacetamide) (2 mL). Under ice cooling, a DMA solution (2 mL) of 2-methyl-1-phenylpropan-2-yl 3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate (895 mg, 2 mmol) was slowly added to the solution, and the mixture was stirred for 30 minutes. After that, a DMA solution (2 mL) of 2-chloro-3-nitro-5-trifluoromethylpyridine (454 mg, 1 Eq) was slowly added, and the mixture was stirred at room temperature for 4.5 hours. Water and 3 N hydrochloric acid were added to the reaction mixture, and ethyl acetate extraction was performed. The organic layer was concentrated and the residue was subjected to column chromatography to give the desired compound, i.e., 2-methyl-1-phenylpropan-2-yl 3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate (653 mg, containing about 20% nitropyridine (starting material)).

According to the analysis of related databases, 72587-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; Yonemura, Ikki; Sano, Yusuke; Suwa, Akiyuki; Fujie, Shunpei; US2018/352811; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1289093-31-7, 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. 1289093-31-7, name is 5-Bromo-3-chloro-2-isobutoxypyridine. A new synthetic method of this compound is introduced below.

Preparation 32: 3-Chloro-2-isobutoxy-5-(4 A5,5-tetramethyl-H ,3,21dioxaborolan-2- -pyridine; Method (i):; To a dry flask was added 5-bromo-3-chloro-2-isobutoxy-pyridine [preparation 30] (825mg, 3.12mmol), KOAc (918mg, 9.35mmol), bis- pinocolatodiboronate (989mg, 3.90mmol) and Pd(dppf)2CI2 (127mg, 0.156mmol) followed by DMF (10ml). The mixture was degassed twice by evacuating and filling with nitrogen and heated at 80C for 6 hours under nitrogen. The reaction mixture was partitioned between EtOAc (30ml) and water (30ml), and the organics washed with brine (20ml), dried over MgS04, filtered and concentrated in vacuo. Purification by column chromatography (ISCO Companion, 40g, heptane – 30% EtOAc:heptane) gave the desired product as a colourless oil (227mg).1 H NM (400 MHz, CDCI3) delta ppm 1 .04 (d, J=6.64 Hz, 6 H) 1 .34 (s, 12 H) 2.09 – 2.21 (m, 1 H) 4.18 (d, J=6.64 Hz, 2 H) 7.97 (d, J=1 .56 Hz, 1 H) 8.37 (d, J=1 .56 Hz, 1 H) impurities present

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1289093-31-7, 5-Bromo-3-chloro-2-isobutoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; BELL, Andrew Simon; DE GROOT, Marcel John; LEWTHWAITE, Russell Andrew; MARSH, Ian Roger; SCIAMMETTA, Nunzio; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/95781; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78686-79-0, 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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate. A new synthetic method of this compound is introduced below.

Compounds are represented in generic form, with sub stituents as noted in compound descriptions elsewhere herein. A more specific example is set forth below. In one aspect, ethers of type 6.7 can be prepared beginning with the commercially available 5-bromo-2-chloronicotinic acid, which is converted to the corresponding ester by reaction with methanol in the presence of an acid such as hydrochloric acid to yield compound 6.2. Alkylation to provide compound 6.3 is accomplished by use of a Suzuki cross coupling reaction using potassium allyltrifluoroborate in the presence of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II). Reaction with 4-methoxybenzylamine affords compound 6.4. A cross-coupling reaction between compound 6.4 and benzyl alcohol in the presence of CuI, Cs2CO3, and a diamine ligand yields the aryl ether, compound 6.5. The p-methoxybenzyl protecting group is removed using cerium(IV) ammonium nitrate (CAN), followed by reduction of the carbonyl using lithium aluminum hydride. The amide, compound 6.7, is formed by reaction of the 3-(benzyloxy)-5,6,7,8-tetrahydro-1,6-naphthyridine, formed in the previous step, with benzoyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78686-79-0, its application will become more common.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Dawson, Eric S.; US2012/178776; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1111637-68-3, 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 1111637-68-3 as follows.

To a solution of 5-bromo-3-fluoro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.65mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.77 g, 6.98 mmol), potassium acetate (1.37 g, 13.95 mmol) and l, l’-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (340 mg, 0.46mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (240 mg, 20%): NMR (400 MHz, Chloroform-d) delta 11.44 (m, 1H), 8.73 (d, 7= 1.6 Hz, 1H), 8.46 (d, 7= 1.2 Hz, 1H), 7.10 (m, 1H), 1.39 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-68-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55304-75-1, Adding some certain compound to certain chemical reactions, such as: 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine,molecular formula is C6H2Cl2F3N, 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 55304-75-1.

Nine separate sealed tubes, each containing a mixture of 2,6-dichloro-3-(trifluoromethyl)pyridine (10.0g, 46.3 mmol) and ammonium hydroxide (91 g, 100 mL, 2600 mmol) were stirred at 100 C. for 12 h. After cooling to rt, the contents of all of the sealed tubes were combined and the solvents were concentrated in vacuo. Purification of the (FCC, SiO2; 5-20% EtOAc/petroleum ether) afforded the title compound as a colorless oil (57 g, 66%), which solidified upon standing. MS (ESI): mass calcd. for C6H4ClF3N2, 196.0; m/z found, 196.8 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.69 (d, J=8.0 Hz, 1H), 6.42 (d, J=8.4 Hz, 1H), 5.01 (br s, 2H).

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. 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 131803-48-0, Adding some certain compound to certain chemical reactions, such as: 131803-48-0, name is Methyl 6-(bromomethyl)nicotinate,molecular formula is C8H8BrNO2, 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 131803-48-0.

NaH (60%, 41.5mg, 1 .O4mmol) was added to a solution of (3) (200mg, 0.99mmol) in DMF (lOmL) at 5C under N2(g). The reaction mixture was stirred for 20 mm then methyl 4-(bromomethyl)benzoate (294mg, 1 .29mmol) was added. The stirring was continued at 70C under N2(g) for lh. The reaction was cooled to rt and poured onto water (l5OmL) and brine (5OmL), the aqueous was extracted with EtOAc (3 xlOOmL). Combined organics were dried over Na2504, filtered and concentrated invacuo. The residue was purified by flash column chromatography withCH2CI2/EtOAc (1:0-0:1) then EtOAc/MeOH (1:0-4:1) to yield (4) (251mg, 73%).1H NMR (500 MHz, Chloroform-d), OH ppm: 8.06-8.10 (m, 2H), 7.87-7.92 (m, 3H),7.78 (d, J=1.5 Hz, 1H), 7.44 (d, J=8.4 Hz, 2H), 7.23 (dd, J=8.2, 1.4 Hz, 1H), 7.15(dd, J=8.1, 4.7 Hz, 1H), 5.42 (5, 2H), 3.85 (5, 3H), 3.73 (5, 3H). LCMS (ES): Found 350.9 [M+H].

According to the analysis of related databases, 131803-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/181137; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 942947-94-6, 5-Bromo-4-chloropyridin-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, 942947-94-6, blongs to pyridine-derivatives compound. Computed Properties of C5H4BrClN2

Synthesis of 4-chloro-5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-2- pyridylamine[00100] To a dry 500-mL flask was added 5-bromo-4-chloro 2-pyridylamine (7.3 g, 35.8 mmol), potassium acetate (10.3 g, 105 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (10.1 g, 39.8 mmol) and dioxane (150 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (0.85 g, 1.04 mmol) was added. The reaction was refluxed in a 1 15 C oil bath for 6 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was then added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were concentrated and the crude material was purified by Si02 chromatography (EtOAc as eluent). Upon removal of solvent, 3: 1 hexanes/CH2Cl2 was added (100 mL). After soni cation, the resulting solid was filtered and concentrated in vacuo yielding 2.8 g of a white solid. By ¾ NMR the material was a 10: 1 mixture of boronate ester and 2-amino-4-chloropyridine byproduct. The material was used as is in subsequent Suzuki reactions. LCMS (m/z):173 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). ¾ NMR (CDCI3): delta 8.36 (s, 1H), 6.46 (s, 1H), 4.70 (bs, 2H), 1.38 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942947-94-6, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 104830-06-0, 2-Amino-3-iodopyridine, 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: 2-Amino-3-iodopyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Amino-3-iodopyridine

2-bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine- 2 obtained in Step 5 of Intermediate Synthesis Example 1 -yl] ethan-1-one and 19 ml of acetonitrile was added 1.39 g of 3-iodopyridin-2-amine at room temperature. The reaction mixture was stirred under heating reflux for 9 hours. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (100 ml). The obtained organic layer was dehydrated with anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 2.0 g of the objective compound as a brown solid.

The synthetic route of 104830-06-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ??????????; Tsuji Keisuke; Kudo Takao; Maizuru Yukihiro; Noto Kenkichi; Dai ? Nishi ? Atsuko; Matsui Yo Jin; Kobayashi Masaki; Kon Naka Hotaka; (136 pag.)JP2018/70585; (2018); 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. 950670-18-5, name is 3-Bromo-5-fluoropicolinonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C6H2BrFN2

To a suspension of 6-cyclopropyl-2-[(3R)-piperidin-3-yl]-1,2-dihydroisoquinolin-1-one (100.0 mg, 0.33 mmol) in DMF (2 mL) DIPEA (0.2 mL, 0.99 mmol) and 3-bromo-5- fluoropyridine-2-carbonitrile (75 mg, 0.36 mmol) were added. The mixture was stirred at 90C for 3 h, and then it was purified by silica NH flash chromatography with 20 to 100% ethyl acetate in cyclohexane to give 3-bromo-5-[(3R)-3-(6-cyclopropyl-1-oxo-1,2-dihydroisoquinolin- 2-yl)piperidin-1-yl]pyridine-2-carbonitrile (126.0 mg, 85% yield) as a white solid. MS found for C23H21BrN4O as (M+H)+ 449.1, 451.1.

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, 950670-18-5, 3-Bromo-5-fluoropicolinonitrile.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem