Day: April 12, 2022

Electric Literature of 1060814-91-6 ,Some common heterocyclic compound, 1060814-91-6, molecular formula is C9H10BrNO2, 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 ethyl 2-(4-bromopyridin-2-yl)acetate (1.72 g, 7.05 mmol) in THF (23.49 ml) was added dropwise LDA(4.05 ml, 8.10 mmol, 2M solution in THF) and the resulting mixture was stirred for 40 mm at-78C. Allyl bromide (0.610 ml, 7.05 mmol) was added dropwise, and the stirring was continuedat -78C for 2h and checked by LCMS (little desired product). The reaction mixture was slowly warmed to RT and stirred at RT for lhr (the reaction complete). The reaction was quenched by adding a saturated aqueous solution of NH4C1 (20 mL). The aqueous layer was extracted with Et20 (2 x 20 mL), the organic phases were combined, washed with HC1 (1 M, 20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash column chromatography on silica gel (1/1 EtOAc/Hex) to give the titlecompound. LC/MS = 285.77 [M+lj

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. 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92276-38-5, Adding some certain compound to certain chemical reactions, such as: 92276-38-5, name is 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine,molecular formula is C5H3BrN4, 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 92276-38-5.

General procedure: To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).v [000223] Step 2: A 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 40%) was obtained as a solid using a procedure analogous to that described in Step 3 of Example4, substituting the product obtained from Step 1 of this example for the 2-chloro-6,7- dimethoxyquinoxaline used in Example 4 and substituting 2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (Ref: S. Abraham et al, WO 2011022473 Al) for the 2-(2-fluoro-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)-N-(5 -(1 -(trifluoromethyl)cyclopropyl)isoxazol-3 -yl)acetamide used in Example 4. LC-MS (ESI) mlz 561 (M+H).[000224] Step 3: To a 1:1 mixture of N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 – yl)-2-(4-(l -((2-(trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5 -b]pyridin-6- yl)phenyl)acetamide and N-(5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)-2-(4-(3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo [4,5 -b]pyridin-6-yl)phenyl)acetamide (71 mg, 0.127 mmol) was added trifluoroacetic acid (5 mL), and the mixture was stirred at rt for 1 h. The mixture was concentrated under reduced pressure and the residue was purified by reverse-phase preparative HPLC using a mixture of water (containing 5% CH3CN and 0.05% HCOOH) and CH3CN (containing 0.05% HCOOH) as the mobile phase and Varian Pursuit XRs diphenyl column as the stationary phase to afford 2-(4-(3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)phenyl)-N- (5 -(1,1,1 -trifluoro-2-methylpropan-2-yl)isoxazol-3 -yl)acetamide (12 mg, 22%) as a solid. ?H NMR (500 MHz, DMSO-d6) oe 11.41 (br s, 1H), 9.00 (d, J= 2.0 Hz, 1H), 8.60 (br s, 1H), 7.80 (d, J 8.5 Hz, 2H), 7.48 (d,J 8.5 Hz, 2H), 6.95 (s, 1H), 3.77 (s, 2H), 1.53 (s, 6H); LC-MS (ESI) m/z 431 (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. 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine, molecular formula is C6H6N2O2, 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.

Example 1; Scheme A; A mixture of a-1 (0.0072 mol) and paraformaldehyde (0.0058 mol) in DMSO (3.5ml) and triton B (0.27ml) was stirred at 90C for 4 hours, then cooled to room temperature and purified by column chromatography over silica gel (eluent: CH2CI2 then CH2CI2/ CH3OH/NH4OH (99/1/0.1); 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.3 g of intermediate a-2 (20%).

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 18699-87-1, 2-Methyl-3-nitropyridine.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1448427-99-3, Adding some certain compound to certain chemical reactions, such as: 1448427-99-3, name is 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine,molecular formula is C10H13N5, 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 1448427-99-3.

5-(4-Cyclopropyl-1H-imidazol-1-yl)-2-fluoro-4-methylbenzoic acid hydrochloride (30 g,102 mmol) was suspended in anhydrous 1,2-dichioromethane (900 mL) at room temperature. Oxalyl chloride (18 ml, 205 mmol) was added while stirring under nitrogen, followed by N,N25 dimethylformamide (0.783 ml, 10.2 mmol). The mixture was stirred for about 4 hr at roomtemperature, and then the solvent was removed under reduced pressure. The residue was dissolved in about 600 mL anhydrous dichloromethane. 6-(4-Isopropyl-4H-1,2,4-triazol-3- yl)pyridin-2-amine (22.9 g, 113 mmol) and 4-dimethylaminopyridine (12.5g, 102 mmol) were rapidly added with stirring under nitrogen. The reaction was stirred for about 2 hours at roomtemperature and the dichioromethane was evaporated. The residue was dissolved in 500 mL water and solid NaHCO3 was added until the pH of the mixture was about 7. DichiOromethane was added (about 500 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 300 mL). The combined organics were washed with water (2 x 200 mL),dried over MgSO4, filtered and concentrated. The residue was dissolved in a minimum amount of THF, and water was added slowly until a thick slurry was formed. The solids were collected by filtration, washed with water, and dried.The solids obtained (about 72 g) were recrystallized from hot EtOH (Smug solid) and the solids collected by filtration, washed with 2:1 diethyl ether/EtOH, followed by diethyl ether and dried

According to the analysis of related databases, 1448427-99-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; ANDRES, Mark; CARRA, Ernest, A.; CHAN, Brenda, J. Burke; CHIU, Anna; LAPINA, Olga, Viktorovna; LATHROP, Stephen, P.; SMOLENSKAYA, Valeriya; YU, Lok, Him; (187 pag.)WO2016/105453; (2016); A1;,
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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-chloro-6-picoline

Example 633-[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-6-methyl-2-pyridinecarboxylic acidCla)2-Chloro-5-(2-chloro-6-methyl-3-pyridinyl)-JV-(tricyclo[3.3.1.13’7]dec-l-ylmethyl)-benzamideA mixture of [4-chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid (Example 2 (a)) (174 mg), 3-bromo-2-chloro-6-methyl-pyridine (104 mg),potassium carbonate (138 mg) and Z?w(triphenylphosphine)palladium(II) chloride (27 mg)in tetrahydrofuran (2 mL) and water (2 mL) was stirred at room temperature under anitrogen atmosphere over 72 hours. The mixture was filtered through diatomaceous earth,washing with methanol, and the filtrate was concentrated in vacuo. Purification bychromatography (SiOa, zsohexane:emyl acetate 1:1 as eluant) gave the sub-title compoundas a solid (135 mg).MS: APCI(+ve) 429/431 (M+H*)

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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3430-21-5, 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 3430-21-5 as follows.

Step-I: 6-Amino-5-methyl-pyridine-3-carbonitrile To a mixture of DMF:water (100:2, 102 mL) was added 5-bromo-3-methyl-pyridin-2-amine (10 g, 53.47 mmol), zinc cyanide (3.77 g, 32.1 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene (3.56 g, 6.4 mmol) and degassed for 20 mins. To this was added tris(dibenzylideneacetone)dipalladium (0) (2.45 g, 2.67 mmol) and heated at 120 C. After stirring for 16 h, reaction mixture was cooled to room temperature. To it was added mixture of saturated solution of ammonium chloride: ammonium hydroxide:water (4:1:4, 100 mL). Slurry formed was cooled to 0 C. and again mixture of saturated solution of ammonium chloride: ammonium hydroxide:water (4:1:4, 100 mL) added and stirred for 1 h. Solid formed was filtered through Buchner funnel and dried under high vacuum to get 6.0 g (81%) of titled compound as a tan solid. MS (ES) m/z 134.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-21-5, its application will become more common.

Reference:
Patent; Kharul, Rajendra; Bhuniya, Debnath; Mookhtiar, Kasim A.; Singh, Umesh; Hazare, Atul; Patil, Satish; Datrange, Laxmikant; Thakkar, Mahesh; US2015/65464; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 947249-27-6 , The common heterocyclic compound, 947249-27-6, name is 2-Bromo-3-(difluoromethoxy)pyridine, molecular formula is C6H4BrF2NO, 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.

Preparation 1032-Cvclopropyl-3-(difluoromethoxy)pyridineCyclopropylboronic acid (383 mg, 4.5 mmol) and potassium phosphate tribasic (1 .89g, 8.9 mmol) were added to a solution of 2-bromo-3-difluoromethoxypyridine (Preparation 102, 570 mg, 2.5 mmol). The mixture was heated to 80 C and degassed thoroughly by bubbling nitrogen through the mixture. After 30 minutes, the reaction was heated to 95 C and tricyclohexylphosphine (84 mg, 0.30 mmol) was added followed by palladium acetate (32 mg, 0.14 mmol). The reaction was stirred at 95 C for 18 hours then cooled to room temperature. The mixture was filtered through arbocel, washing with EtOAc and the filtrate concentrated in vacuo. The residue was then purified by flash column chromatography eluting with EtOAc:heptane 1 :5 to afford the title compound as a colourless oil (273 mg, 58%).1H NMR (400 MHz; DMSO-d6): delta 0.95 (m, 4H), 2.30 (m, 1 H), 7.05-7.42 (t, 1 H), 7.15 (m,1 H), 7.5 (m, 1 H), 8.25 (m, 1 H).LCMS Rt = 2.09 minutes MS m/z 186 [MH]+

The synthetic route of 947249-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan Daniel; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/7869; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 947249-13-0, 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.947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, molecular formula is C6H5BrF2N2O, molecular weight is 239.02, as common compound, the synthetic route is as follows.

A mixture of 5-bromo-3-(difluoromethoxy)pyridine-2-amine (88 mg, 0.37 mmol), bis(pinacolato)diboron (102 mg, 0.40 mmol), potassium acetate (0.215 mg, 2.2 mmol), and Pd(dppf)-CH2Cl2 (30 mg, 0.037 mmol) in dry dioxane (2.0 mL) was sparged with argon, and heated at 120 C. for 30 min. After cooling to rt, the reaction mixture was centrifuged and the supernatant decanted, and used in the next step without further purification: LCMS (m/z, MH+, boronic acid): 205.0, tR=0.27 min.

Statistics shows that 947249-13-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-(difluoromethoxy)pyridin-2-amine.

Reference:
Patent; Huang, Zilin; Jin, Jeff; Machajewski, Timothy; Antonios-McCrea, William R.; McKenna, Maureen; Poon, Daniel; Renhowe, Paul A.; Sendzik, Martin; Shafer, Cynthia; Smith, Aaron; Xu, Yongjin; Zhang, Qiong; Chen, Zheng; US2013/210818; (2013); 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 880870-13-3

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mE) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, succes30 sively. The resulting suspension was stirred at 95 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to providethe crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate/hexanes to afford theproduct.?H NMR (500 MHz, DMSO-d5), oe 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); EC/MS (M+1)=169.

The synthetic route of 880870-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Walsh, Shawn P.; Pasternak, Alexander; Shi, Zhi-Cai; Cato, Brian; Kim, Esther Y.; (32 pag.)US9493474; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1019021-85-2, 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 1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a stirring suspension of 6-fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (150 mg, 0.833 mmol) in anhydrous dichloromethane (3 ml_) at 0 C under argon was added dropwise oxalyl chloride (74 muIota_, 0.874 mmol). Then, a drop of anhydrous DMF was added and the reaction mixture was stirred at 0 C for 1 .5 hours. The solvent was concentrated and the crude solid was added to a stirring solution of methyl (3-(3-amino- 4-methylphenyl)-1 ,2,4-oxadiazol-5-yl)methylcarbamate (155) (120 mg, 0.416 mmol) in anhydrous pyridine (3 mL) at 0 C. The reaction was stirred at room temperature under argon for 20 minutes. The solvent was concentrated and the crude product was purified by silica chromatography to give methyl (3-(3-(6-fluoroimidazo[1 ,2-a]pyridine-3- carboxamido)-4-methylphenyl)-1 ,2,4-oxadiazol-5-yl)methylcarbamate (F167). 1 H NMR (400MHz, c/6-DMSO) delta 10.12 (s, 1 H), 9.48 – 9.46 (m, 1 H), 8.63 (s, 1 H), 8.07 (t, J = 5.6 Hz, 1 H), 8.06 (d, J = 1 .6 Hz, 1 H), 7.90 – 7.86 (m , 1 H), 7.82 (dd, J = 2.0, 8.0 Hz, 1 H),7.67 – 7.62 (m, 1 H), 7.50 (d, J = 8.0 Hz, 1 H), 4.57 (d, J = 6.0 Hz, 2H), 3.59 (s, 3H), 2.36 (s, 3H). MS m/z 425.39 (M+1 )+.

According to the analysis of related databases, 1019021-85-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem