Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 188057-20-7, 4-Iodopyridin-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, 188057-20-7, blongs to pyridine-derivatives compound. Application In Synthesis of 4-Iodopyridin-3-ol

To a degassed solution of 3b (150 mg, 0.50 mmol) and a 1-halo, 2-hydroxy or thio-aryl compound (e.g., 4-iodo-3- pyridinol, 261 mg, 1.5 mmol) in DMF (5 ml) was added(with protection from light) triethylamine (0.28 ml, 2.0mmol), followed by Cul (38 mg, 0.2 mmol) and thentetrakis(triphenylphosphine)palladium (116 mg, 0.1 mmol). After sealing the reaction vessel with a rubber septum, the reaction mixture was heated in an oil bath at 40 C. for 18h. After concentrating, the methanol extract was filtered andthe filtrate chromatographed, using an elution gradient of CHCl/MeOH (95/5-90/10). Example 9 (X, YN, ZCl,R?NH2, R2, R3, R4, R7, R8H, R5, R6OH, R9CH2OH,24 mg) was recovered as yellow crystals after recrystallizing from MeOH. Analysis calculated for C,7H,8C1N504.0. 1 MeOH. 1.1 5i02: C, 44.70; H, 4.04; N, 15.24. Found: C, 44.72; H, 4.20; N, 15.24.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188057-20-7, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp.; Southern Research Institute; Arasappan, Ashok; Njoroge, F. George; Kwong, Cecil D.; Ananthan, Subramaniam; Bennett, Frank; Velazquez, Francisco; Girijavallabhan, Vinay M.; Huang, Yuhua; Kezar, III, Hollis S.; Maddry, Joseph A.; Reynolds, Robert C.; Roychowdhury, Abhijit; Fowler, Anita T.; Secrist, III, John A.; Kozlowski, Joseph A.; Shankar, Bandarpalle B.; Tong, Ling; Kim, Seong Heon; MacCoss, Malcolm; Venkatraman, Srikanth; Verma, Vishal; (798 pag.)US9433621; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 886365-47-5, Adding some certain compound to certain chemical reactions, such as: 886365-47-5, name is 1-(5-Bromo-2-chloropyridin-3-yl)ethanone,molecular formula is C7H5BrClNO, 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 886365-47-5.

A mixture of compound5(1.0 g, 4.26 mmol) and guanidine carbonate(1.04 g, 8.52 mmol) in DMA (25 mL) was stirred at 135Cfor 3hours. After cooling, the reaction mixture wasdiluted withwater(100 mL) and extracted with ethyl acetate (50 mL×3).The combined organic layers werewashed with water (50 mL×2) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol/ammonium hydroxide=400:10:1, v/v) to give the title compound6as a brown solid(340 mg, 42% yield). 1H NMR (300 MHz, DMSO-d6) delta 8.87 (d,J= 2.6 Hz, 1H), 8.61 (d,J= 2.6 Hz, 1H), 7.29 (brs, 2H), 2.72 (s, 3H).

According to the analysis of related databases, 886365-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Fangbin; Lin, Songwen; Liu, Peng; Tao, Jing; Yi, Chongqin; Xu, Heng; Bioorganic and Medicinal Chemistry Letters; vol. 24; 18; (2014); p. 4538 – 4541;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 127446-34-8, 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. 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide. A new synthetic method of this compound is introduced below.

To a solution of Lambda/-(6-chloro-3-formylpyridin-2-yl)pivalamide (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 niL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (10O mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6JV EtaC1 (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 00C and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+Eta+] for C8H4N2OClF.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/116337; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80537-07-1, 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 80537-07-1 as follows.

2-Phenylpyrazolo[1,5-a]pyridine An o-dichlorobenzene solution (42 mL) of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid (10.0 g) was stirred at 160C for 2 hours under an argon atmosphere. The reaction solution was evaporated under vacuum and the obtained solid was washed with n-hexane to obtain a title compound as a brown solid (9.45 g). 1H-NMR (400 MHz, CDCl3) delta 6.72 (1H, td, J = 7.3,1.2 Hz), 6.79 (1H, s), 7.05-7.11 (1H, m), 7.18-7.21 (2H, m), 7.34-7.39 (1H, m), 7.44-7.49 (1H, m), 7.97 (2H, d, J = 7.3 Hz), 8.47 (1H, d, J = 7.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,80537-07-1, its application will become more common.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1167056-96-3, 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 1167056-96-3, name is 3-Bromo-5-chloro-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 3-bromo-5-chloro- 1H- pyrrolo[2,3-c]pyridine (AJ-2) (2.9 g, 12.6 mmol) in anhydrous DMF (100 mL) was added 2- chloro-6-(trifluoromethyl)benzoyl chloride (4.6 g, 18.9 mmol) and NaH (60%) (1 g, 25.2 mmol). The solution was stirred at room temperature for 2 hours. The solution was quenched with H2O(400 mL). The suspension was extracted with EtOAc (150 mL x 3). The combined organic layer was washed with H2O(100 mL x 2) and brine (100 mL x 2) and dried over anhydrous Na2SO4. The solution was evaporated and dried over vacuo and 5.7 g product was obtained. LCMS (ESI) calc?d for C15H6BrCl2F3N2O [M+H]+: 437, found: 437.

According to the analysis of related databases, 1167056-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan; WO2014/28589; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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.

Example 325e 5-Bromo-1,3-dimethyl-1H-pyrazolo[3,4-c]pyridine 325e and 5-Bromo-2,3-dimethyl-2H-pyrazolo[3,4-c]pyridine 326a A mixture of 325d (3.0 g, 14.2 mmol), CH3I (2.40 g, 17.0 mmol), and K2CO3 (2.9 g, 21.3 mmol) in acetonitrile (60 mL) was stirred at 30C for 1 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 8:1 petroleum ether/ethyl acetate to afford 325e (920 mg, 29.0%) as a white solid, and eluting with 2:1 petroleum ether/ethyl acetate to afford 326a (390 mg, 12.0%) as a gray solid. MS-ESI: [M+H]+ 226.1.

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1227502-35-3, 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 1227502-35-3 as follows.

5-bromo-3-(hydroxymethyl)pyridin-2(lH)-one (34.1 mg, 0.167 mmol) was stirred with iodomethane (30.5 mu, 0.201 mmol) and potassium carbonate (115 mg, 0.836 mmol) in DMF (557 mu) in a 2-dram vial containing a Teflon-coated stir bar at room temperature for 1 h. Additional DMF (1.0 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 19 h. The reaction mixture was partitioned between water and ethyl acetate (~4 mL total volume), and the aqueous phase was extracted with ethyl acetate (3×2.5 mL). The combined organic phases were extracted with brine (2×2 mL), then dried over sodium sulfate and filtered. Excess solvent was evaporated from the filtered organic phase to afford 5-bromo-3-(hydroxymethyl)-l- methylpyridin-2(lH)-one (17.7 mg, 0.073 mmol, 43.7% yield) as a clear, pale yellow oil. LCMS MH+: 217.9. HPLC Ret. Time 0.51 min. Method Bl . NMR (400 MHz, CHLOROFORM-d) delta 7.42 (s, 2H), 4.57 (d, J=6.2 Hz, 2H), 3.56 (s, 3H), 3.41 (t, J=6.4 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227502-35-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; HAQUE, Tasir Shamsul; WHITELEY, Brian K.; GILMORE, John L.; (192 pag.)WO2019/28302; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109306-86-7 ,Some common heterocyclic compound, 109306-86-7, molecular formula is C11H8BrN, 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) 2-[2-(2-Pyridyl)-phenyl thio]-benzoxazole 2-Mercapto benzoxazole (604 mg; 4 mmole) was reacted with 2-(2-bromophenyl)pyridine (936 mg; 4 mmole) in the presence of KOH (224 mg; 4 mmole) in N-methyl pyrrolidine (16 ml). The mixture was heated under reflux for 6 hours, worked up and flash chromatographed (silica), using ethyl acetate/petroleum ether (2/3) eluant to give the sub-title compound as a pale brown oil (52 mg; 4.3%). m/z 304, 281, 277, 271, 186 (Base Peak), 154, 135.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109306-86-7, its application will become more common.

Reference:
Patent; Fisons plc; US4900751; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

(B) 6-iodo-5-methylimidazo[1,2-a]pyridine (0308) To a solution of 5-iodo-6-methylpyridin-2-amine (7.5 g, 32 mmol) in ethanol (400 mL) was added 2-chloroacetaldehyde aqueous solution (18 mL, 40%), and the mixture was stirred at 80 C for 16 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, neutralized with 30% aqueous sodium hydroxide solution, and extracted with dichloromethane (150 mL×3). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.0 g). MS: [M+H]+ 259.1

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, 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 C13H17NO4, blongs to pyridine-derivatives compound. Computed Properties of C13H17NO4

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem