Month: April 2022

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. 1239880-00-2, name is 6-Bromoimidazo[1,5-a]pyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H5BrN2

Synthesis of 6-bromoimidazo[1,5-a]pyridine-1-carbaldehyde. A solution of 6-bromoimidazo[1,5-a]pyridine (1.7 g, 8.63 mmol) in dry DMF (944 mg, 12.9 mmol) was cooled in an ice bath to 0-5 C. Phosphorus oxychloride (1.98 g, 12.9 mmol, 1.5 eq) was added dropwise at 0-5 C. and the reaction mixture was subsequently stirred at 100 C. over 2 h. The reaction mixture was cooled and poured onto aqueous saturated sodium bicarbonate (200 mL), kept stirring for another 2 h, and extracted with ethyl acetate (50 mL*3). The combined organic phases were washed with brine and dried over sodium sulphate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=1/1) to afford 6-bromoimidazo[1,5-a]pyridine-1-carbaldehyde (500 mg, yield: 26%) as a yellow solid. ESI-MS [M+H]+: 226.0.

The synthetic route of 1239880-00-2 has been constantly updated, and we look forward to future research findings.

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

Reference of 75073-11-9 ,Some common heterocyclic compound, 75073-11-9, molecular formula is C6H7IN2, 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-Iodo-6-methylpyridin-2-amine (361 mg, 1.54 mmol), DMF (6.17 mL), tribasic potassium phosphate (655 mg, 3.08 mmol), and N,iV-dimethylethylenediamine (27 mg, 0.31 mmol) were added to a microwave vial. The vial was then flushed and purged 3 times with argon before adding copper(I) iodide (1 mg, 0.077 mmol). The vial was again flushed and purged 3 times with argon and was then sonicated for 30 minutes. The vial was heated for 2 hours at 200C via microwave irradiation, cooled to room temperature, and then again heated for 16 hours at 200C via microwave irradiation. The reaction mixture was filtered and purified by reverse phase HPLC (5-30% acetonitrile/water with 0.1% TFA, linear gradient) to afford a mixture of 6-methylpyridin-2-amine TFA salt, 6-methyl-5-(2H-l,2,3-triazol-2-yl)pyridin-2- amine TFA salt and 6-methyl-5-(lH-l,2,3-triazol-l-yl)pyridin-2-amine TFA salt that was subsequently used without further purification. MS ESI calc’d. for CgHjoNs [M + H]+ 176, found 176.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75073-11-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; BIENSTOCK, Corey, E.; BUTCHER, John, W.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; DONOFRIO, Anthony; ELLIS, John Michael; FISCHER, Christian; HAIDLE, Andrew, M.; JEWELL, James, P.; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETERSON, Scott, L.; SMITH, Graham Frank; WO2013/52394; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 957187-27-8, 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. 957187-27-8, name is 8-Bromo-6-chloroimidazo[1,2-a]pyridine. A new synthetic method of this compound is introduced below.

A 50-mL round-bottomed flask equipped with a reflux condenser was charged with 8-bromo-6-chloroimidazo[1,2-a]pyridine 101a (264 mg, 1.14 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (328 mg, 1.14 mmol), Pd2(dba)3 (102 mg, 0.11 mmol), Xantphos (63 mg, 0.11 mmol), Cs2CO3 (3.58 g, 11.0 mmol), dioxane (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100 C. overnight. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:50 methanol/dichloromethane to afford 121a as an orange solid (290 mg, 66%). MS-ESI: [M+H]+385.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,957187-27-8, its application will become more common.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one, molecular formula is C5H3ClN2O3, 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.

4-Chloro-2-hydroxy-5-nitropyridine (17.2 g, 98.6 mmol) was suspended in toluene (150 mL) before careful addition of phosphorus oxychloride (28 mL, 300 mmol) over 20 minutes. The reaction mixture was heated to reflux for 6 h before cooling to 60 C and stirring for a further 15 h. The reaction mixture was cooled to ambient temperature and then concentrated to dryness under vacuum to give a dark brown oil which was carefully basified at 0 C with sat. K2CO3 (?60 mL). The mixture was extracted with AcOEt (3 x 200 mL). The combined organic phases were quickly washed with water and then brine before drying over Na2SO4. The solvents were removed under vacuum to give a dark brown oil which was purified by passing through a plug of silica, (eluting with petrol ? 1:1, petrol: AcOEt) to give the product as a pale yellow powder (12.2 g, 64%). 1H NMR (400 MHz, CDCl3) delta (ppm): 9.0 (1 H, s), 7.6 (1 H, s). LC-MS: Rt = 2.44 min.

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 850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel (Prof. Dr.); Falcenberg, Mathias (Dr.); EP2818472; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 81565-19-7, 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 81565-19-7 as follows.

(3) The title compound was obtained from 3-chloro-4- trifluoromethylpyridine by the method described in Eur . J . Org . Chem., (2004), 3793.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81565-19-7, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; WO2008/18639; (2008); 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. 56057-19-3, name is 6-Chloro-5-nitro-2-picoline, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Chloro-5-nitro-2-picoline

Method B applied to 2-chloro-6-methyl-3-nitropyridine (86 mg, 0.5 mmol) and 5-phenylcarbamoyl-pentanoic acid methyl ester (141 mg, 0.6 mmol) afforded the title compound as viscous oil (61 mg, 38%). 1H NMR (DMSO) delta 1.52-1.73 (m, 4 H), 2.22 (t, J = 6.8 Hz, 2 H), 2.48 (s, 3 H), 2.75 (t, J = 6.8 Hz, 2 H), 3.53 (s, 3 H), 7.13 (d, J = 8.0 Hz), 7.47-7.63 (m, 5 H), 7.93 (d, J = 8.0 Hz).

The synthetic route of 56057-19-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; sanofi-aventis; EP1878724; (2008); 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. 133081-25-1, name is 6-(2-(tert-Butoxycarbonyl)hydrazinyl)nicotinic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 6-(2-(tert-Butoxycarbonyl)hydrazinyl)nicotinic acid

4. Synthesis of ((3aR, 4R, 6R, 6aR)-6-(7-allyl-2 -amino-6, 8-dioxo-], 6,7,8-tetrahydropurin-9-yl)-2, 2-dimethyl-tetrahydrofuro[3, 4-dill, 3]dioxol-4-ylfrnethyl 6-(2- (tert-butoxycarbonyl)hydrazinyl)nicotinate To a suspension of 6-(2-(tert-butoxycarbonyl)hydrazinyl)nicotinic acid (668 mg,2.63 mmol) in toluene (10 mL, anhydrous) was added 2,4,6-trichlorobenzoyl chloride(959 mg, 3.95 mmol) and DIPEA(679 mg, 5.62 mmol). The suspension was stirred for10 mm and then a suspension of 7-allyl-2-amino-9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3 ,4-dj [1 ,3]dioxol-4-yl)- lil-purine6,8(711,9H)-dione (500 mg,1.32 mmol) and DMAP (321 mg, 2.63 mmol) in toluene (10 mL, anhydrous) was added. The suspension was stirred for 15 hrs then quenched with brine. The aqueous phase was extracted with EtOAc (20 mL*3). The organic phase was combined, dried over Na2504, filtered and concentrated. The residue was purified byreverse phase biotage to give a white solid product (390 mg, 48%).

The synthetic route of 133081-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASCEND BIOPHARMACEUTICALS PTY LTD; PIETERSZ, Geoffrey, Alan; WO2013/67597; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1211517-76-8, 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 1211517-76-8, name is 3-Bromo-5-fluoro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: A mixture of the intermediate of step 1 (150 mg, 475 pmol), 3-bromo-5-fluoro-4-methylpyridine(108 mg, 570 pL), Cu(l)l (6 mg, 24 pmol), K2C03 (132 mg, 964 pmol) and N,N?-dimethyl ethylendiamine(30 mg, 81 pmol) in toluene (0.5 mL) was heated in a sealed tube to 120 C under N2 atmosphereovernight. The volatiles were removed under reduced pressure and the residue was purified bychromatography (Interchim cartridge 5OSiHP /12 g, EtOAc/Cy) to yield the title compound of example17(111 mg,55%).LC-MS (Method 2): m/z [M-?-H] = 425.1(MW calc. = 424.76); R = 0.79 mm. Step 2: A mixture of the intermediate of step 1 (150 mg, 475 pmol), 3-bromo-5-fluoro-4-methylpyridine(108 mg, 570 pL), Cu(l)l (6 mg, 24 pmol), K2C03 (132 mg, 964 pmol) and N,N?-dimethyl ethylendiamine(30 mg, 81 pmol) in toluene (0.5 mL) was heated in a sealed tube to 120 C under N2 atmosphereovernight. The volatiles were removed under reduced pressure and the residue was purified bychromatography (Interchim cartridge 5OSiHP /12 g, EtOAc/Cy) to yield the title compound of example17(111 mg,55%).LC-MS (Method 2): m/z [M-?-H] = 425.1(MW calc. = 424.76); R = 0.79 mm.

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 1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; VOSS, Felix; WACHTEN, Sebastian; KLESS, Achim; RITTER, Stefanie; WO2015/90580; (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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine, molecular formula is C6H6F3N3, 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. Formula: C6H6F3N3

Production Example 59-4 6.1 g of sodium hydrogen sulfite was added to a mixture of 8.6 g of 5-trifluoromethyl-pyridine-2,3-diamine, 11 g of 2-formyl-5-trifluoromethylphenyl ethyl sulfide, and 67 mL of DMF at room temperature. After heating and stirring the mixture for 3 hours at 100C. 1 g of copper (II) chloride dihydrate was added thereto, and the mixture was heated and stirred for 1 hour at 100C. After allowing the mixture to cool to room temperature, the reaction mixture was added to water and was subjected to extraction using ethyl acetate. A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure. The residue was subjected to silicagel column chromatography to obtain yellow solid powder. The powder was washed with hexane to obtain 12 g of 2-(2-ethylsulfanyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as the present condensed heterocyclic compound 59).

With the rapid development of chemical substances, we look forward to future research findings about 107867-51-6.

Reference:
Patent; Sumitomo Chemical Company, Limited; SUZUKI, Tatsuya; IWATA, Atsushi; NOKURA, Yoshihiko; EP2865266; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 3430-21-5 ,Some common heterocyclic compound, 3430-21-5, 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.

6-Amino-5-methylnicotinonitrile. A mixture of 2-Amino-5-bromo-3-methylpyridine (15.49 g, 82.8 mmol) and Cu(I)CN (9.27 g, 103.5 mmol) in DMF (160 mL) was heated at 150 C. for 24 h. The reaction mixture was poured onto water and the solid which formed was extracted by using ethylacetate (600 mL, 3 times) from aq. NH4OH. The solvent was evaporated and the precipitate purified by chromatography (SiO2, hexanes/EtOAc 4:6). Yield 70%, mp 198-200 C., (Lit. mp 203-205 C.; see Dunn A. D. and Norrie R. J. Prakt. Chem./Chem.-Ztg, 338 (7), 663-666 (1996). Lit. melting point not reported via palladium-catalyzed cyanation; see Maligres, P. et al., Tetrahedron Lett., 40, 8193-8195 (1999).

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. 3430-21-5, 5-Bromo-3-methylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boykin, David W.; Tidwell, Richard R.; Wilson, W. David; Ismail, Mohamed A.; US2005/282853; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem