Tag: M.W:200-300

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

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

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

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

Synthetic Route of 2808-86-8, 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.2808-86-8, name is 2,3,4,5-Tetrachloropyridine, molecular formula is C5HCl4N, molecular weight is 216.8801, as common compound, the synthetic route is as follows.

With a thermometer, reflux condenser,300 g of 2-chloropyridine was added to a 500 mL glass reaction vial of a chlorine tube.15g supported catalyst Sn-AC, heated to 110 C,Chlorine gas (pressure 0.1MPa) was introduced at a flow rate of 200 ml/min, and after 20 hours of reaction, the temperature was lowered to 30 C or lower.Filter to remove the supported catalyst,The obtained filtrate (HPLC detection of 2,3,4,5-tetrachloropyridine was 217 g) was placed in a glass reaction flask.And adding methanol-water mixed solvent 800mL (volume ratio 4:1),79 g of pyridine and 217 mg of activated carbon catalyst loaded with Pd (purchased from Xi’an Kaili New Materials Co., Ltd., grade 5% palladium carbon Pd/C, the same below), and the reaction system was repeatedly replaced with hydrogen three times.Then, it was heated to 50 C, and hydrogen gas (pressure 0.5 MPa) was introduced at a flow rate of 200 ml/min.At the same time, a 5% aqueous solution of Na2CO3 was added dropwise to maintain the pH of the reaction system at 8-10.HPLC analysis showed that the content of 2,3,4,5-tetrachloropyridine in the material was less than 5%, and the hydrogen was stopped.The material is lowered to normal temperature. The catalyst was filtered, and the filtrate was evaporated under reduced pressure to remove methanol, and the precipitated white solid was collected by filtration.The filter cake was washed three times with 100 mL of 5% hydrochloric acid and dried to give 465 g of white solid.HPLC analysis showed that the crude product contained 5.8% dichloropyridine and 89.8% 2,3,5-trichloropyridine.2,3,4,5-tetrachloropyridine 4.4%. The crude product was subjected to distillation under reduced pressure to obtain 414 g of 2,3,5-trichloropyridine (yield: 86.2%).The purity is greater than 99%.

Statistics shows that 2808-86-8 is playing an increasingly important role. we look forward to future research findings about 2,3,4,5-Tetrachloropyridine.

Reference:
Patent; Yancheng Heng Sheng Chemical Co., Ltd.; Huan Bin; Li Yong; Zhang Xiaohang; Cheng Ronghua; (9 pag.)CN108341767; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 69422-72-6, name is 2,4,6-Trichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H2Cl3NO2

A solution of the product of EXAMPLE 11 C (1.5 g, 6.7 mmol) in dichloromethane (50 mL) was treated at room temperature with 2 drops of N, N-dimethylformamide. Oxalyl chloride (1.27 g, 10 mmol) was added dropwise over 15 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. Ammonium (gas) was passed through a solution of the acid chloride in tetrahydrofuran (20 mL) and the mixture stirred at room temperature for 0.5 hours. The mixture was concentrated under vacuum and the residue purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 225 (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, 69422-72-6, 2,4,6-Trichloronicotinic acid.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97683; (2012); 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. 3430-23-7, name is 3,5-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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. Application In Synthesis of 3,5-Dibromo-4-methylpyridine

To a stirred solution of 3,5-dibromo-4-methylpyridine (2.0 g, 7.97 mmol) in dry N,N-dimethylformamide (10 mL) was added copper cyanide (1.07 g,l 1.95 mmol) at room temperature . The reaction mixture was heated at 150 C for 6 h, cooled it, quenched with water (5 mL) and extracted with 50% ethyl acetate/hexane (2 x 100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. MS (M+l): 199.1.

With the rapid development of chemical substances, we look forward to future research findings about 3430-23-7.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1086381-43-2 ,Some common heterocyclic compound, 1086381-43-2, molecular formula is C8H10BrN, 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.

Step 4: To a vial containing palladium(II) acetate (4.3 mg, 0.019 mmol) and butyldi-1-adamantylphosphine (13.9 mg, 0.039 mmol) was added 1,4-dioxane (300 ul). The vial was evacuated and refilled with Ar (3*). The solution was warmed to 70 C. for 20 minutes. In a separate vial were combined pivalic acid (9.9 mg, 0.097 mmol), cesium fluoride (44 mg, 0.29 mmol), 2-bromo-4-isopropylpyridine (purchased from CombiPhos Catalysts, Inc.) (29 mg, 0.15 mmol), (R)-4-((1-cyclobutylethyl)amino)-7-methyl-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (40 mg, 0.097 mmol) and 1,4-dioxane (0.5 mL). The mixture was degassed with Ar for 15 minutes, and the catalyst solution was added to the mixture. The resulting mixture was stirred at 130 C. for 3 days. The mixture was cooled to room temperature and concentrated. The residue was dissolved in DCM and purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to give (R)-4-((1-cyclobutylethyl)amino)-2-(4-isopropylpyridin-2-yl)-7-methyl-3-(4-(trifluoromethyl)benzyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc’d for C30H31F3N6 [M+H]+ 533. found 533.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1086381-43-2, its application will become more common.

Reference:
Patent; Christopher, Matthew P.; Fradera Llinas, Francesc Xavier; Machacek, Michelle; Martinez, Michelle; Reutershan, Michael Hale; Shizuka, Manami; Sun, Binyuan; Thompson, Christopher Francis; Trotter, B. Wesley; Voss, Matthew E.; Altman, Michael D.; Bogen, Stephane L.; Doll, Ronald J.; US2014/179680; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 62150-47-4, Ethyl 4-bromopicolinate, 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, 62150-47-4, blongs to pyridine-derivatives compound. Product Details of 62150-47-4

A solution of ethyl 4-bromo-2-picolinate (1e) (92%, 20.6 g, 82.3 mmol) and acetone (2.43 mL, 32.9 mmol) in DME (100 mL) was added dropwise to a stirred suspension of NaH (60% suspension in oil, 6.6 g, 165 mmol) in DME (100 mL) under an atmosphere of argon at room temperature. The temperature was slowly increased until reflux was achieved, and a vigorous evolution of gas was observed after 10 min and the brown suspension turned dark red. The reaction mixture was allowed to cool to room temperature and was stirred for 2 h. The solvent was removed in vacuo and the red-orange paste slowly treated with water (200 mL). The resultant insoluble mixture was acidified as described in previously to pH 6.5 and the copious amount of yellow solid so obtained was collected by filtration and washed with water until the washing appeared colourless. The solid was oven-dried under vacuum (40C, ca. 30 mm) for 2 days to yield the crude triketone 5e as a yellow solid (15.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62150-47-4, its application will become more common.

Reference:
Article; Lin, Chih-Pei; Florio, Pas; Campi, Eva M.; Zhang, Chunfang; Fredericks, Dale P.; Saito, Kei; Jackson, W. Roy; Hearn, Milton T.W.; Tetrahedron; vol. 70; 45; (2014); p. 8520 – 8531;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

To a solution of 2,6-dibromo-4-methyl-pyridine (5.1 g, 20.4 mmol) and 4-[l-(4-Methoxy-benzyl)-l H-pyrazol-4-yl]-pyridin-2-ylamine (5.2 g, 18.6 mmol) in dioxane (150 mL) was added sodium tert-butoxide (1.96 g, 20.4 mmol) and then l, l ‘-bis(di-t- butylphosphino)ferrocene palladium dichloride (1.2 g, cat.) was added. The mixture was degassed by nitrogen for 3 times and then refluxed for 15h. The mixture was partitioned between water and EtOAc, and the organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via flash- chromatography on silica gel (30 % EtOAc in petroleum ether) to give (6-Bromo-4-methyl- pyridin-2-yl)- {4-[l-(4-methoxy-benzyl) -lH-pyrazol-4-yl]-pyridin-2-yl}-amine (3.0 g, yield 36.1 %) as a light yellow solid. MS ESI calc’d. For: C22 H20BrN5O [M + H]+ 450, found 450.

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ANDRESEN, Brian, M.; ANTHONY, Neville, J.; MILLER, Thomas, A.; WO2014/74422; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem