Tag: M.W:200-300

Electric Literature of 13626-17-0, 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. 13626-17-0, name is 3,5-Dibromo-4-chloropyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3,5-dibromo-4-chloropyridine (X, 0.5 g, 1.84 mmol) and cyclopropylboronic acid (0.17 g, 2.02 mmol), cesium carbonate (1.19 g, 3.68 mmol ) in the mixture of 1,4-dioxan (10 mL) and water (2 mL).The reaction mass was purged with nitrogen for 15 min. Then catalyst Pd (dppf)2Cl2 (0.075 g, 0.09 mmol) was added and allowed to stir at 100 C for 4 h. The reaction mixture was filtered through celite bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts were concentrated under vacuum to afford the crude compound, which was purified by column chromatography using 10-40% ethyl acetate/hexane as an eluent to obtain title compound. MS (M+l): 233.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13626-17-0, 3,5-Dibromo-4-chloropyridine, and friends who are interested can also refer to it.

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

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

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

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

Electric Literature of 1227270-32-7, 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 1227270-32-7 as follows.

In a vial, 2-iodo-1H-pyrrolo[2,3-b] pyridine 18a (200 mg, 0.82 mmol, 1 eq.) was dissolved in 8 ml of acetonitrile. Then 0.4 ml of acetic acid followed by 182 mg of Eschenmoser’s salt (0.98 mmol, 1.2 eq.) were added. After sealing the vial, the reaction mixture is stirred for 20 h at room temperature. 15 ml of a 2M solution of potassium hydroxide is added slowly and then the organic phase was extracted with ethyl acetate (3×20 ml). The organic phases are combined and then dried over MgSO4, filtered through cotton and evaporated to dryness. Finally, the crude is triturated with pentane and then vacuum filtered to obtain compound 174 (190 mg, 77%) as a yellow solid. Rf=0.10 (methanol/dichloromethane=2/98) mp=142-144 C. IR (v, cm-1, neat) 2957, 2932, 2851, 2812, 2768, 1603, 1580, 1514, 1489, 1448, 1407, 1369, 1354, 1328, 1287, 1273, 1248, 1206, 1167, 1147, 1121, 1094, 1036, 1004, 978, 905, 842. 1H NMR (400 MHz, CDCl3, 20 C.) delta 13.08 (s1, 1H), 8.41 (dd, J=4.9, 1.4 Hz, 1H), 8.09 (dd, J=7.9, 1.4 Hz, 1H), 7.11 (dd, J=7.9, 4.8 Hz, 1H), 3.60 (s 2H), 2.33 (s, 6H). 13C NMR (101 MHz, CDCl3, 20 C.) delta 151.0 (Cq), 142.0 (CH), 127.4 (CH), 121.3 (Cq), 116.7 (Cq), 115.8 (CH), 82.9 (Cq) 56.1 (CH2), 45.4 (2×CH3). HRMS (+ESI) calculated for C10H12IN3 (M+H+): 302.0148, found: 302.0148.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227270-32-7, its application will become more common.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE D’ ORLEANS; UNIVERSITE FRANCOIS RABELAIS DE TOURS; CENTRE HOSPITALIER REGIONAL UNIVERSITAIRE DE TOURS; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE; ROUTIER, Sylvain; SUZENET, Franck; CHALON, Sylvie; BURON, Frederic; VERCOUILLIE, Johnny; MELKI, Ronald; BOIARYNA, Liliana; GUILLOTEAU, Denis; PIERI, Laura Ronald; (144 pag.)US2019/211011; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7477-10-3 , The common heterocyclic compound, 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, molecular formula is C6H3ClN2O4, 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 solution of compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid.4.2.4.5 5-Nitro-6-(4-pyrimidin-2-ylpiperazin-1-yl)nicotinic acid (6e) Procedure A was used with compound 5 (170 mg, 0.84 mmol) and 1-(2-pyrimidyl)piperazine (278 mg, 1.7 mmol) to afford product 6e as a yellow solid (106 mg, 38%). 1H NMR (300 MHz, CDCl3) delta: 8.83 (d, J = 2.1 Hz, 1H), 8.56 (d, J = 2.1 Hz, 1H), 8.41 (d, J = 8.4 Hz, 2H), 6.70 (t, J = 4.8 Hz, 1H), 3.90-3.86 (m, 4H), 3.66-3.62 (m, 4H). ESI-MS: m/z (329, MH-).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909187-64-0, 6-Benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3(2H)-one, 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, 909187-64-0, blongs to pyridine-derivatives compound. Product Details of 909187-64-0

A mixture of 6-benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-ol (2.00 g, 8.72 mmol) and palladium on carbon (0.200 g, 1.88 mmol, Aldrich) in MeOH (100 mL) was stirred under H2 atmosphere for 48 h. The mixture was filtered through Celite and the filter cake was washed with MeOH. The mixture was concentrated in vacuo. The filter cake was washed with water and the filtrate was concentrated in vacuo. Both fractions contained the title compound. MS (ESI, pos. ion) m/z: 140 (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,909187-64-0, its application will become more common.

Reference:
Patent; Amgen Inc.; US2006/199817; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Formula: C6H8BrN3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

Step 3. 5-bromo-N3-isopropyl-N2-methylpyridine-2.3-diamine and 6-bromo-2,2,3-trimethyl-2.3-dihydro- 1H-imidazor4.5-blpyridine; 5-bromo-N2-methylpyridine-2,3-diamine (54.4 mg, 0.269 mmol) was dissolved in isopropyl acetate (1.5 ml) and acetone (23 mul, 0.31 mmol), trifluoroacetic acid (0.045 ml, 0.58 mmol), and sodium triacetoxyborohydride (64 mg, 0.30 mmol) were added. The reaction was stirred under nitrogen at room temperature for 4 hours, and then more acetone was added (0.040 ml) along with TFA (0.090 ml) and isopropyl acetate (0.5 ml). The reaction was then stirred overnight. This reaction was repeated on a larger scale using 5-bromo-N2-methylpyridine-2,3-diamine (288 mg, 1.43 mmol), 2,2,2-trifluoroacetic acid (0.30 ml, 3.9 mmol), acetone (0.13 ml, 1.8 mmol), and sodium triacetoxyborohydride (352 mg, 1.66 mmol). Then, both reactions were poured into water (25 ml), and solid sodium hydroxide was added to raise the pH to about 10. The layers were separated, and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum. To afford 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine and 6-bromo-2,2,3- trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine (399 mg, 97% combined yield). 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine: MS (ESI pos. ion) m/z: 244 (MH+, 79Br), 246 (MH+, 81Br). Calculated exact mass for C9H14BrN3 243 (79Br), 245 (81Br). 6-bromo-2,2,3-trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine: MS (ESI pos. ion) m/z: 242 (MH+, 79Br), 244 (MH+, 81Br). Calculated exact mass for C9H12BrN3 241 (79Br), 243 (81Br).

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 178876-83-0, Methyl 6-amino-3-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, Computed Properties of C7H7BrN2O2, blongs to pyridine-derivatives compound. Computed Properties of C7H7BrN2O2

Example 57D methyl 3-bromo-6-fluoropicolinate To a solution of nitrosonium terafluoroborate (17.8 g) in dichloromethane (100 mL) at 5 C. was added EXAMPLE 57C (26.1 g) in dichloromethane (250 mL) over 1 hour. The reaction mixture was stirred an additional 30 minutes at 5 C., and allowed to warm to room temperature overnight. The reaction mixture was quenched with pH 7 buffer (100 mL), and neutralized with solid potassium carbonate. The resulting mixture was extracted with ether (twice), and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed on silica gel using 1-10% ethyl acetate in hexanes to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178876-83-0, Methyl 6-amino-3-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1052714-48-3, name is 6-Bromo-3-fluoropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Bromo-3-fluoropicolinic acid

6-Bromo-3-fluoro-2-methylpyridine (5 g, 26.3 mmol) was dissolved in 100 ml of water and potassium permanganate (12.5 g, 78.9 mmol) was added. The reaction mixture was heated to reflux for 12 h. Solid constituents were removed by filtration. The filter cake was washed three times with 100 ml of water. The collected wash solutions were concentrated and the crude product was obtained as white solid, which was further reacted directly. The crude product (6 g) was dissolved in 20 ml of dimethylformamide and, after adding sodium ethanethiolate (6.6 g, 78.9 mmol), the mixture was stirred for 12 h at room temperature. The reaction mixture was filtered and the organic phase was concentrated. The residue was purified by chromatography (mobile phase: water/acetonitrile) and the product was obtained in the form of a yellow solid. log P (neutral): 1.79; MH+: 262; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 7.85-7.39 (m, 2H), 3.34-2.92 (m, 2H), 1.39-1.15 (m, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1052714-48-3.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHSAFT; FISCHER, RUEDIGER; WILCKE, DAVID; KAUSCH-BUSIES, NINA; HAGER, DOMINIK; ILG, KERSTIN; HOFFMEISTER, LAURA; WILLOT, MATTHIEU; PORTZ, DANIELA; GOERGENS, ULRICH; TURBERG, ANDREAS; (161 pag.)US2018/271099; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem