Tag: M.W:200-300

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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C10H9BrN2O2

Ethyl 5 -bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (0.100 g, 0.372 mmol), 1- methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (0.101 g, 0.483mmol) and XPhos-Pd G3 (7.9 mg, 9.3 jimol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuumlAr), then THF (2 mL) and potassium phosphate tribasic (0.5 M aq.) (1.12 mL, 0.557 mmol) were added. The reaction mixture was degassed again, and stirred at 100 C for 1 h. Solvent was removed under reduced pressure. The obtained residue was dissolved in MeOH (1.0 mL)/THF (1.0 mL), and LiOH (1 M aq.) (1 .12 mL, 1.12 mmol) was added. The reaction mixture was stirred under microwave irradiation at 120 C for 15 mm. The mixture was acidified with TFA, the solvent was removed under reduced pressure, the residue was purified by preparativeHPLC to afford Intermediate 39 (0.055 g, 61% yield) as an off-white solid. MS(ESI) m/z:243.0 (M+H) ?H NMR (500MHz, DMSO-d6) oe ppm 8.81 (dd, J=7.2, 0.8 Hz, 1H), 8.43(s, 1H), 8.33 (s, 1H), 8.10 (dd,J=1.9, 0.8 Hz, 1H), 8.05 (s, 1H), 7.36 (dd,J=7.3, 2.1 Hz,1H), 3.90 (s, 3H).

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, 885276-93-7, Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175205-81-9 ,Some common heterocyclic compound, 175205-81-9, molecular formula is C6H3BrF3N, 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.

General procedure: a. Palladium(0)-catalyzed reactions. A Schlenk flask was charged with Pd(dba)2 (1-8 mol %, 2.9-23 mg), phosphine ligand (1.25-9 mol %), and bromopyridine2-8 (0.5 mmol), and 5 mL of dioxane, amine 1 or 21 (0.625 mmol), and sodium tert-butoxide(0.75 mmol, 72 mg) were added. The mixture was refluxed for 12 h with stirring and cooled to room temperature, the organic phase was separated, the precipitate was washed with methylene chloride (5 mL),and the organic phase was combined with the washings and evaporated under reduced pressure. The residue was dissolved in methylene chloride (5 mL), and the solution was washed with water (3 × 5 mL), dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). b. A Schlenk flask was charged with copper(I)iodide (10 or 20 mol %, 9.5 or 19 mg), 2-isobutyrylcyclohexanone(20 or 40 mol %, 17 or 34 mg), and bromopyridine 2-8 (0.5 mmol), and 1 mL of DMF,amine 1 or 21 (0.5 mmol), and cesium carbonate(0.75 mmol, 250 mg) were added. The mixture was heated for 24 h at 140C with stirring and cooled to room temperature, the organic phase was separated,and the residue was washed with methylene chloride(5 mL). The organic phase was combined with the washings and evaporated under reduced pressure, the residue was dissolved in methylene chloride (5 mL),and the solution was washed with water (3 × 5 mL),dried over 4A molecular sieves, and thoroughly evaporated under reduced pressure (1 mm). The spectral parameters of compounds 9, 16 [21], 22, and 29 [26]were consistent with published data

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175205-81-9, its application will become more common.

Reference:
Article; Lyakhovich; Murashkina; Averin; Abel; Maloshitskaya; Savelyev; Orlinson; Beletskaya; Russian Journal of Organic Chemistry; vol. 55; 6; (2019); p. 737 – 747; Zh. Org. Khim.; vol. 55; 6; (2019); p. 829 – 840,12;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59786-31-1, 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. 59786-31-1, name is Methyl 3-bromoisonicotinate. A new synthetic method of this compound is introduced below.

Example 68 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(piperidin-4-ylamino)isonicotinamide Compound 118a. To a stirred solution of methyl 3-bromoisonicotinate (0.500 gm, 2.3148 mmol, 1 equiv) & tert-butyl 4-aminopiperidine-1-carboxylate (0.463 gm, 2.3148 mmol, 1 equiv) and CS2CO3 (1.5 gm, 4.6296 mmol, 2 equiv) in dioxane (15 mL). The resulting mixture was purged with nitrogen for 10 min followed by addition of Pd2(dba)3 (0.106 gm, 0.1157 mmol, 0.05 equiv) and xantphos (0.134 gm, 0.2314 mmol, 0.1 equiv), again purged with nitrogen for 10 min. The reaction mixture was heated at 120 C. for overnight. The progress of reaction was monitored by LCMS. The reaction mixture was diluted with water (30 mL), extracted with EtOAc (2*50 mL). The combined organic layers were washed with water (30 mL), with brine (30 mL), dried over Na2SO4, concentrated to afford the crude which was purified by flash chromatography to obtain methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinate (400 mg, 51.49%) as a white solid. LCMS: 336.3 [M+H]+ 1H NMR: (400 MHz, DMSO-d6) delta 8.41 (s, 1H), 7.60-7.51 (m, 2H), 7.27 (d, J=7.9 Hz, 1H), 3.00 (m., 4H), 2.04-1.88 (s, 3H), 1.44-1.35 (s, 9H), 1.31-1.12 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59786-31-1, Methyl 3-bromoisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99368-67-9, Adding some certain compound to certain chemical reactions, such as: 99368-67-9, name is 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine,molecular formula is C6H2ClF3N2O2, 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 99368-67-9.

2-chloro-5-nitro-3-(trifluoromethyl) pyridine 4 (1.57g, 6.93mmol) was dissolved in tetrahydrofuran(THF) (10 ml), then was added to THF (20 ml) suspension of Raney -Ni (200 mg).Hydrogen gas was gentle foaming passing through a 24 hour stirring solutionusing a balloon. The mixture was filtered throughCelite (registered trademark) (World Minerals Inc., Lompoc, CA) and the solventwas evaporated under reduced pressure to obtain 6-chloro-5- (trifluoromethyl)pyridin-3-amine 5.

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. 99368-67-9, 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, MICHAEL E; SAWYERS, CHARLES L; OUK, SAMEDY; TRAN, CHRIS; WONGVIPAT, JOHN; (40 pag.)JP2016/11315; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1050501-88-6, 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. 1050501-88-6, name is 2-Bromo-6-chloropyridin-3-amine. A new synthetic method of this compound is introduced below.

A solution of 2-bromo-6-chloropyridin-3-amine (5 g, 24.1 mmol) and potassium thiocyanate (7 g, 72.3 mmol) in ethanol (50 ml_), hydrochloric acid (37 %, 100 mL) was added and the reaction mixture was stirred at 100 C for 40-45 h. The completion of the reaction was confirmed by TLC. The reaction mixture was cooled to room temperature and concentrated to provide a brown solid, which was partitioned in dichloromethane (150 mL) and aqueous 1 N NaOH (50 mL). The solid was filtered and dried to provide the crude title compound as a light yellow solid (3.5 g, 79 %). The product was taken as such for next step.MS: 186.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1050501-88-6, its application will become more common.

Reference:
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (0 pag.)WO2019/233883; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117519-08-1, Adding some certain compound to certain chemical reactions, such as: 117519-08-1, name is 2-Chloro-3-nitro-6-(trifluoromethyl)pyridine,molecular formula is C6H2ClF3N2O2, 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 117519-08-1.

A solution of 2-chioro-3-nitro-6-(trifiuoromethyl)pyridine (2.0 g, 8.8 mmoi) and 6-aninobenzo[d]thiazoi-2(3H?)-one (1.5 g, 8.8 mmol) in DMF (40 ml.) was heated at 110 0Q After 3h. sodium dithionite (6.1 g, 35.3 mmoi) was added to the mixture was let stir at 110 cc for 5 h. Thereaction was diluted with water (320 mL) and let stir for 20 mm where precipitate formed. Thereaction was filtered and the solid was washed with H20 and oven dried at 45 C to give the desiredcompound as a solid (2.6 g, 90%). MS (ESI): mass caicd. for C,3HF3N4OS, 326.05 rn/z found, 327.0 [M++{]t.

According to the analysis of related databases, 117519-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1035123-89-7, 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. 1035123-89-7, name is 3-(6-Bromopyridin-3-yl)acrylic acid, molecular formula is C8H6BrNO2, 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.

Step 3: 3-(6-Bromo-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (63 mg, 0.219 mmol) was suspended in THF and treated with triethylamine (25 mg, 0.241 mmol) and then the resulting mixture was stirred for 10mins. 3-(6-Bromo-pyridin-3-yl)-acrylic acid (50 mg, 0.219 mmol) was added to the reaction mixture followed by DMTMM (66 mg, 0.241 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat’d NaHCO3 (x2), and brine, and then dried over anhyd. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized (EtOAc/n-Hexane) to yield the title compound (71 mg, 72 %). 1H NMR (300 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.77 (t, 1H, J = 6.0 Hz), 8.60 (d, 1H, J = 2.4 Hz), 7.96 (dd, 1H, J = 8.1, 1.8 Hz), 7.70 (d, 1H, J = 8.1 Hz), 7.48 (d, 1H, J = 15.9 Hz), 7.28 (s, 1H), 7.27 (d, 1H, J = 8.7 Hz), 6.81 (d, 1H, J = 15.9 Hz), 4.50 (s, 1H), 4.39 (d, 2H, J = 5.7 Hz), 3.06 (s, 3H). ESI [M+H]+; 452.0.

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 1035123-89-7, 3-(6-Bromopyridin-3-yl)acrylic acid.

Reference:
Patent; Amorepacific Corporation; EP1882687; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65001-21-0, 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.65001-21-0, name is 5-Bromopyridine-3-sulfonyl chloride, molecular formula is C5H3BrClNO2S, molecular weight is 256.51, as common compound, the synthetic route is as follows.

Step 3 – Preparation of 3-[l-(5-bromo pyridine-3-sulfonyl)-5-chloro-lH-indol-3-yl] propionic acid methyl ester (11); [0176] Into a flask, 3-(5-chloro-lH-indol-3-yl)-propionic acid methyl ester (11, 150 mg, 0.00063 mol), and tetrabutyl ammonium hydrogen sulfate were dissolved in 20 mL of dichloromethane and 20 mL of 50% KOH solution was added. The solution was mixed vigorously and 5-bromo- pyridyl-3-sulfonyl chloride (10, 240 mg, 0.00095 mol) was slowly added to the reaction. After 5-6 minutes of vigorous stirring, precipitates began to form. An additional 3-4 mL of 50% KOH was added and the reaction was stirred overnight. TLC (30% ethyl acetate/hexane) showed that the starting material had disappeared. The reaction mixture was extracted with 3 x 50 mL of dichloromethane and the organic layers were combined and washed with water, brine, and dried over MgSO4. The organic layer was filtered and roto evaporated to half its volume. Silica was added and the solvent completely removed. Chromatography was run using a gradient solvent condition of 0 to 20% ethyl acetate/hexane over 15 minutes, then 20 to 45% over 15 minutes. The desired compound was isolated. 1H NMR consistent with structure.

Statistics shows that 65001-21-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyridine-3-sulfonyl chloride.

Reference:
Patent; PLEXXIKON, INC.; WO2008/109700; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13959-02-9, 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 13959-02-9, name is 3-Bromoisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 33methyl 3-bromoisonicotinate H2SO4 (0.5 mL) was added to a solution of 3-bromoisonicotinic acid (500 mg, 2.48 mmol) in MeOH (10 mL). The resulting solution was heated at reflux overnight. The mixture was cooled to 0° C. and a solution of 5percent NaHCO3 (5 mL) was added. The aqueous layer was basified to pH=7-8 with 50percent aqueous NaOH. It was then extracted with DCM (3.x.). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford title crude product (465 mg, 87percent) as an oil. 1H NMR (300 MHz, CDCl3) delta ppm 3.96 (s, 3H) 7.61 (d, J=5.10 Hz, 1H) 8.61 (d, J=5.10 Hz, 1H) 8.85 (s, 1H).

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 13959-02-9, 3-Bromoisonicotinic acid.

Reference:
Patent; ASTRAZENECA AB; US2010/130477; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13959-02-9, 3-Bromoisonicotinic 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, 13959-02-9, blongs to pyridine-derivatives compound. Quality Control of 3-Bromoisonicotinic acid

General procedure: To a solution of Intermediate 7 (110 mg, 0.37 mmol), 3-methoxybenzene-1,2- diamine (50 mg, 0.34 mmol) and DIPEA (0.2 mL, 1 mmol) in DMF (2 mL) was added HATU (160 mg, 0.41 mmol). The reaction mixture was stirred at r.t. for 48 h, then partitioned between DCM and water. The organic phase was separated, then dried and concentrated in vacuo. The crude residue was purified by flash column chromatography (0-100% EtOAc/hexanes) to give the title compound (28.7 mg, 20%) as a white solid. LCMS (Method 5): [M+H]+ m/z 415, RT 1.31 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13959-02-9, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; FOULKES, Gregory; FROST, James Richard; HORSLEY, Helen Tracey; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; REUBERSON, James Thomas; SCHULZE, Monika-Sarah Elisabeth Dorothea; TAYLOR, Richard David; YAU, Wei Tsung; ZHU, Zhaoning; (246 pag.)WO2019/138017; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem