Day: April 8, 2022

Electric Literature of 1072-98-6 ,Some common heterocyclic compound, 1072-98-6, molecular formula is C5H5ClN2, 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 of 2-amino-5-chloropyridine (2.0 g, 16 mmol) [Matrix Scientific, 021118] in acetone (39 mL) was treated with ethyl bromopyruvate (2.2 mL, 16 mmol) and heated at 60 C for 45 min. The reaction mixture was cooled to 20 C and the suspension was filtered. The solid that was collected was washed with a small amount of cold acetone and dried in vacuo. The solid was diluted with ethanol (12 mL) and water (19 mL), heated at 65 C, and treated with sodium bicarbonate (1.6 g, 19 mmol) portionwise. The reaction mixture was cooled to 20 C and the suspension was filtered. The solid that was collected was washed with water (4 x 80 mL) and dried in vacuo to give the desired product (2.6 g, 74%). LCMS for Ci QHI 0CIN2O2(M+H)+: m/z = 225.1.

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. 1072-98-6, 2-Amino-5-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; LI, Yun-Long; YUE, Eddy W.; SPARKS, Richard B.; WO2011/75643; (2011); 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.1211517-76-8, name is 3-Bromo-5-fluoro-4-methylpyridine, molecular formula is C6H5BrFN, molecular weight is 190.013, as common compound, the synthetic route is as follows.Formula: C6H5BrFN

Step D 3-fluoro-4-methyl-5-f4 A5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl) yridme3-bromo-5-fluoro-4-methylpyridine (9.25 mmol, 2.93 g) bis(pinacolato)diboron (11.10 mmol, 2.82 g) l, -bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.463 mmol, 0.335 g) and potassium acetate (18.50 mmol, 1.816 g) were combined in dioxane (37.0 mL) and heated to 80 C for 24 hours, under nitrogen. The reaction was allowed to cool to room temperature, EtOAc (400ml) added and the mixture filtered through CELITE and washed with 1 :1 saturated sodium bicarbonate solution / water (2 x 200ml) and brine (100ml). Organics were dried over sodium sulphate and solvent evaporated under reduced pressure to yield crude product as a brown oil. Purification by silica chromatography eluting with 25 to 50% EtOAc / heptane afforded 3-fluoro-4-methyl-5-(4J4,5,5-tetramethyl-l.3,2-dioxaborolan-2-yl)pyridine. 1H NMR (CDC13)5: 8.68 (s, IH), 8.39 (s, 1H), 2.48 (s, 3H), 1.38 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HOYT, Scott, B.; PARK, Min, K.; LONDON, Clare; XIONG, Yusheng; BENNETT, D., Jonathan; CAI, Jaiqiang; RATCLIFFE, Paul; COOKE, Andrew; CARSWELL, Emma; MACLEAN, John; SAXENA, Rohit; KULKARNI, Bheemashankar, A.; GUPTA, Archana; WO2012/12478; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1012084-53-5, 5-Bromo-2-fluoropyridin-3-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, Computed Properties of C5H3BrFNO, blongs to pyridine-derivatives compound. Computed Properties of C5H3BrFNO

a)Diisopropylethylamine (0.41 mL, 2.34 mmol) and [2-(chloromethoxy)ethyl](trimethyl) silane (0.32 mL, 1.80 mmol) were added to a solution of 5-bromo-2-fluoropyridin-3-ol (0.30 g, 1.56 mmol) in dichloromethane (8 mL) at 0 C and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was partitioned betweendichloromethane and saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with brine, dried over magnesium sulfate and the solvent was evaporated to dryness. The resulting crude was purified by flash chromatography (gradient from hexanes to diethyl ether) to yield the title compound(0.31 g, 62%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1012084-53-5, 5-Bromo-2-fluoropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); 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. 223463-13-6, name is 5-Bromo-2-iodopyridine, the common compound, a new synthetic route is introduced below. name: 5-Bromo-2-iodopyridine

General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI.

The synthetic route of 223463-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mandali, Pavan Kumar; Chand, Dillip Kumar; Catalysis Communications; vol. 47; (2014); p. 40 – 44;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886365-06-6, 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 886365-06-6 as follows.

General procedure: Into a vial was weighed 1-(5-bromo-4-methylpyridin-2-yl)azetidin-2-one (50 mg, 0.207 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (8.6 mg, 0.0103 mmol), bis(pinacolato)diboron (52.7 mg, 0.207 mmol), and potassium acetate (61.1 mg, 0.622 mmol). Under nitrogen, anhydrous 1,4-dioxane (1.0 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 17 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(1S,2S)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (71.1 mg, 0.207 mmol), chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (8.8 mg, 0.0104 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5.0 mg, 0.0104 mmol), potassium carbonate (86 mg, 0.622 mmol), and water (0.2 mL). The vial was sealed and stirred at 100 C. for 19 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) and then by HPLC to afford the target compound as a white solid (29.6 mg, 31% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.92 (s, 1H), 9.35 (s, 1H), 8.34 (s, 1H), 8.24 (s, 1H), 7.56 (s, 1H), 7.52 (s, 1H), 7.29 (s, 1H), 7.28 (br s, 2H), 6.93 (s, 1H), 3.77 (s, 3H), 3.73 (dd, J=4.7, 4.7 Hz, 2H), 3.12 (dd, J=4.7, 4.7 Hz, 2H), 2.44 (s, 3H), 2.24-2.17 (m, 2H), 1.43-1.33 (m, 1H), 1.23-1.14 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,886365-06-6, its application will become more common.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184416-84-0, Adding some certain compound to certain chemical reactions, such as: 184416-84-0, name is 2,3-Dichloroisonicotinic acid,molecular formula is C6H3Cl2NO2, 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 184416-84-0.

A mixture of 2,3 -dichloroisonicotinic acid (l9.2g, 10 mmol) in BFb/THF (1 M, 300 mL) was stirred at 60 C for 3 h. After cooling to RT, MeOH (100 mL) was slowly added, then the reaction mixture was concentrated and diluted with H20 (100 mL) and extracted with EtOAc (200 mL x 3). The organic layer was separated and washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure to give the crude title compound (15.4 g, yield 87%) as a yellow solid which was used directly without further purification. (0448) [0261] MS (ES+) CeHsChNO requires: 177, found: 178 [M+H]+.

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. 184416-84-0, 2,3-Dichloroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; JONES, Philip; CROSS, Jason; BURKE, Jason; MCAFOOS, Timothy; KANG, Zhijun; (154 pag.)WO2019/213318; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103878-09-7, 3-Ethoxypicolinic acid, 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 3-Ethoxypicolinic acid, blongs to pyridine-derivatives compound. Safety of 3-Ethoxypicolinic acid

EXAMPLE 7 4.0 g of 3-ethoxy-2-pyridinecarboxylic acid and 4.1 g of 1,1′-carbonyldiimidazole were stirred at 70 for 2 hours in 250 ml of tetrahydrofuran. To this solution were then added dropwise 4.1 g of N-(t-butoxycarbonyl)ethylenediamine in 20 ml of tetrahydrofuran and the mixture was left to stir at 70 for a further 2 hours. The reaction mixture was subsequently cooled to room temperature and concentrated to about 1/4 of the volume on a rotary evaporator under reduced pressure, taken up in water and extracted three times with chloroform. The chloroform extracts, dried over magnesium sulfate, were evaporated completely, and the residue was chromatographed on silica gel with 2-5% methanol in methylene chloride as the elution agent and crystallized from methylene chloride/n-hexane, whereby there was obtained t-butyl [2-(3-ethoxypyridine-2-carboxamido)ethyl]carbamate, m.p. 125-126.

The synthetic route of 103878-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4764522; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 696-42-4, 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.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.

To a stirred solution of 5-fluoropyridine-3-carbonitrile (2.0 g, 16.38 mmol) in methanol (20 mL) at RT was added NaOMe (88mg, 1.64 mmol) and the reaction stirred at RT overnight. Ammonium chloride (1 .40g, 26.21 mmol) was added in a single portion and the reaction mixture stirred overnight at RT. The reaction mixture was filtered and the filtrate concentrated to dryness under reduced pressure. The residue was suspended in EtOH (50 mL) and then heated at reflux. The undissolved solid was filtered off and the filtrate concentrated to 1/3 of its volume and then left to stand at RT. The resultant crystals were filtered off, washed with EtOH and air-dried to give the desired product (2.1 1 g, 73%) as white crystals. (0232) 1H NMR (400 MHz, d6-DMSO) delta 8.93 (d, 1 H), 8.88 (s, 1 H), 8.29-8.23 (m, 1 H).

Statistics shows that 696-42-4 is playing an increasingly important role. we look forward to future research findings about 5-Fluoronicotinonitrile.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; BRIGGS, Emma; CARTER, Neil, Brian; MORRIS, Melloney; TATE, Joseph, Andrew; (56 pag.)WO2019/57721; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1064783-29-4, 5-Chloro-3-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, Recommanded Product: 5-Chloro-3-fluoro-2-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 5-Chloro-3-fluoro-2-nitropyridine

5-Chloro-3-fluoro-2-nitropyridine (1 equiv) was dissolved into of anhydrous DIVIF (0.182 M) along with methyl 2-(1 ,4-oxazepan-5-yl)acetate (1.1 equiv) and triethylamine (3 equiv). The mixture was heated to 80 C under an atmosphere of nitrogen with reflux condenser and stirring overnight. After 16 hours the reaction was poured into H20 and extracted three times with EtOAc. Organics were combined, washed with brine, and dried anhydrous Na2SO4. The volatiles were removed and the residue was purified by flash column chromatography over silica gel, eluting with heptane and 0-40% EtOAc gradient to give a yellow oil methyl 2-(4-(5 -chloro-2-nitropyridin-3 -yl)- 1 ,4-oxazepan-5 -yl)acetate in 54.4% yield. LCMS (m/z) (M+H) = 330.1, Rt = 0.91 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1064783-29-4, 5-Chloro-3-fluoro-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); 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. 619331-71-4, name is 4,7-Dibromo-1H-pyrrolo[2,3-c]pyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H4Br2N2

A mixture of 4,7-dibromo-lH-pyrrolo[2,3-c]pyridine (207 mg, 0.75 mmol), 1- tetrahydropyran-2-yl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazole (250 mg, 0.90 mmol), (63 mg, 0.076 mmol), and K2CO3 (0.94 mL, 1.9 mmol, 2.0 M) in DMF (4.0 mL) was stirred at 60 C for 24 h under argon. After cooling, the solvent was evaporated and the residue was chromatographed on a silica gel column (ethyl acetate in dichloromethane 0-100%) to provide 4-bromo-7-(l-tetrahydropyran-2-ylpyrazol-4-yl)-lH-pyrrolo[2,3-c]pyridine (229 mg, 88%). LC-MS 347.1, 349.1 [M+H]+, RT 0.98 min.

The synthetic route of 619331-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem