Tag: M.W=300-400

Adding a certain compound to certain chemical reactions, such as: 401892-47-5, 5-Bromo-2-chloro-4-iodopyridine, 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, 401892-47-5, blongs to pyridine-derivatives compound. name: 5-Bromo-2-chloro-4-iodopyridine

To a stirred solution of 5-bromo-2-chloro-4-iodopyridine (40 g, 126.2 mmol, 1 eq) in DMF (400 mL) was added methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (32.1 mL, 252.5 mmol, 2 eq) followed by CuT (48.2 g, 252.5 mmol, 2 eq). The resulting mixture was heated at 100 C for 6 h. TLC analysis indicated formation of a non-polar spot. The reaction mixture was diluted with water (200 mL), filtered through a celite pad and washed with n-pentane (2 x 500 mL) and followed by cold water (3 x 1000 mL). Organic layers were separated, dried over Na2SO4 and concentrated under reduced pressure at 30 C resulted 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (21 g, 64% yield) as a liquid compound. TLC: 5% EtOAc in pet ether; Rf: 0.7

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,401892-47-5, its application will become more common.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

A sealed tube was charged with 16-1 (1.0 g, 2.70 mmol), Et3N (4.89 mL, 35.1 mmol) and Ethynyltrimethylsilane (4.85 mL, 35.1 mmol) and the resulting solution was degassed with Argon for about 10 minutes followed by the addition of CuI (514 mg, 2.70 mmol) and PdCl2(PPh3)2 (1.89 g, 2.70 mmol). The reaction tube was sealed and heated at 90oC for 16 hours. The reaction was then cooled to room temperature and filtered through a short bed of celite. The filtrate was partitioned between heptane and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The crude mass was dissolved in MeOH (10 mL) and to it was added K2CO3 (713 mg, 5.16 mmol) and the solution was stirred at ambient temperature for 2 hours to produce 16-2. The reaction mass was filtered through a short bed of celite and the filtrate was concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-10% Ethyl acetate in Hexane) to afford 16-2 (462 mg, 1.46 mmol, 54%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 7.63 (d, J = 8.24 Hz, 1H), 7.43-7.28 (m, 10H), 7.34 (d, J = 8.16 Hz, 1H), 5.44 (s, 2H), 5.29 (s, 2H), 3.24 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 915720-71-7, 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. 915720-71-7, name is (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate. A new synthetic method of this compound is introduced below.

In a 5 mL microwave vial a solution of (S)-tert-butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate (60 mg, 0.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (37 mg, 0.24 mmol), Sodium bicarbonate (0.2 mL, 0.4 mmol, 2 M aqueous solution) in Dioxane (2 mL) was bubbled N2 for 3mm then CI2Pd(dppf)CH2CI2 (16 mg, 0.02 mmol) was added. The capped tube was heated to10000 for 16 h. After cooling the reaction mixture was diluted with EtOAc (10 mL) and washed with water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3 x 10 mL). Combined organics were dried over Na2504, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to givea white solid (66 mg, 80% yield). LCMS tR = 1.43 mm; MS mlz 331.1 (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,915720-71-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; CAFERRO, Thomas Raymond; CHEN, Zhuoliang; CHO, Young Shin; COSTALES, Abran Q.; LEVELL, Julian Roy; LIU, Gang; MANNING, James R.; SENDZIK, Martin; SHAFER, Cynthia; SHULTZ, Michael David; SUTTON, James; WANG, Yaping; ZHAO, Qian; WO2014/141104; (2014); 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. 59020-10-9, name is 3-(Tributylstannyl)pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (100 mg) (as prepared in Example 4), 3-(tri-n-butylstannyl)pyridine (442 mg) and DMF (5 ml) was degassed with a stream of N2 for 0.5 h. Bis(triphenylphosphine)palladium(II) chloride (5 mg) was added and the reaction heated to 100 C. for 2 h. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica, eluting with 2.5% MeOH/CH2Cl2 to give the title compound (75 mg, 64%). 1H NMR (400 MHz, CDCl3) ? 8.66 (1H, t, J=3.3 Hz), 8.23 (1H, d, J=1.4 Hz), 7.95-7.92 (1H, m), 7.63 (1H, dd, J=8.0, 1.7 Hz), 7.57-7.54 (2H, m), 7.49-7.38 (5H, m), 4.07 (2H, s), 3.97 (2H, s), 2.73 IS (3H, s), m/z (ES+) 392 (M+H)+.

The synthetic route of 59020-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 858116-66-2, 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.858116-66-2, name is 5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C16H25BrN2Si, molecular weight is 353.3726, as common compound, the synthetic route is as follows.

To a 50 ml reaction flask at room temperature, the compound of formula II (4.08 g, 11.5 mmol) was added, Copper acetylacetonate (0.15g, 0.575mmol), BetaEtaMuRhoO (0.15g, 0 · 575mmol), lithium hydroxide monohydrate (2 · 42g, 57.5mmol), 18ml of DMSO, 4.5ml of water, stirring was turned on, replaced with nitrogen, and the temperature was raised to an internal temperature of 100 C. Temperature reaction for 6 hours. Control raw material reaction is over, stop heating, cool to room temperature (20-30 C), add water 100ml, adjust PH to 6 with 2N dilute hydrochloric acid, precipitation of solids, suction filtration, aqueous phase with ethyl acetate 50ml * 3 Extraction, combining the organic phases, washing once with water and saturated aqueous sodium chloride solution, drying over anhydrous sodium sulfate, and concentrating the solvent to obtain the compound of formula III. Yield: 1.2 g, yield: 78.5%.

The chemical industry reduces the impact on the environment during synthesis 858116-66-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Hongbozhiyuan Pharmaceutical Co., Ltd.; Zhuang Yinqiang; Peng Shaoping; Jiang Hui; (11 pag.)CN107434807; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 578007-66-6, 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. 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-iodo-2-methoxypyridine (50 g, 159 mmol) in toluene (1000 mL) was added phenylmethanethiol (17.8 g, 143 mmol), DIPEA (55.6 mL, 319 mmol), XantPhos (7.37 g, 12.74 mmol). The mixture was degassed with argon for 10 mm then Pd(dba)2 (4.58 g, 7.96 mmol) was added and the reaction mixture was stirred at 70 C for 1 h. The reaction mixture was filtered through celite,washing with EtOAc (200 mL) and the filtrate was concentrated in vacuo. The crude material was purified by normal phase column chromatography on silica eluting with 5% EtOAc in petroleum ether. The appropriate fractions were combined and concentrated in vacuo to afford the title compound (90 g) as a solid.LCMS (Method D) Rt = 2.68 mi [M+H] = 308.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 915720-71-7, Adding some certain compound to certain chemical reactions, such as: 915720-71-7, name is (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate,molecular formula is C12H17BrN2O2, 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 915720-71-7.

Intermediate 67: (5)-tert-butyl (1 -(5-(4-fl uoro-3-methylphenyl)pyridin-2-yI)ethyl)carbamate In a 5 mL microwave vial a solution of (5)-tert-butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate(60 mg, 0.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (37 mg, 0.24 mmol), Sodiumbicarbonate (0.2 mL, 0.4 mmol, 2 M aqueous solution) in Dioxane (2 mL) was bubbled N2 for 3mm then CI2Pd(dppf)CH2CI2 (16 mg, 0.02 mmol) was added. The capped tube was heated to100C for 16 h. After cooling the reaction mixture was diluted with EtOAc (10 mL) and washedwith water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3 x 10 mL). Combined organics were dried over Na2504, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to give a white solid (66 mg, 80% yield). LCMS tR = 1.43 mm; MS m/z 331.1 (M+H).

According to the analysis of related databases, 915720-71-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CHO, Young Shin; LEVELL, Julian Roy; LIU, Gang; SHULTZ, Michael David; VAN DER PLAS, Simon Cornelis; WO2014/141153; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 928653-73-0 ,Some common heterocyclic compound, 928653-73-0, molecular formula is C5H2BrClIN, 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 1 : Sodium hydride (2.0 equiv.) was added to dioxane (0.3 M). 2- ((tetrahydro-2H-pyran-2-yl)oxy)ethanol (2.0 equiv.) was added and the mixture was stirred for 30 min at rt. 5-bromo-2-chloro-3-iodopyridine (1.0 equiv.) was added to the mixture and the reaction was heated to 105 C for 1 hour. The cooled reaction mixture was quenched by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography over silica gel (heptanes with 10% ethyl acetate) to give 5-bromo-3-iodo-2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy )pyridine as a colorless oil in 78% yield. LCMS (m/z) (M+H) = 427.8/429.8, Rt = 1.12 min.

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. 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; LOU, Yan; NISHIGUCHI, Gisele A; RAMURTHY, Savithri; RICO, Alice C.; RAUNIYAR, Vivek; SENDZIK, Martin; SUBRAMANIAN, Sharadha; SETTI, Lina Quattrocchio; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (307 pag.)WO2016/38582; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1198416-32-8, 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.1198416-32-8, name is 2-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C14H11BrN2O2S, molecular weight is 351.22, as common compound, the synthetic route is as follows.

A mixture of 209-3 (30 g, 0.085 mol), methanol (85OmL) and aqueous potassium hydroxide (5 mol/L, 100 mL) was heated under reflux overnight. The majority of the solvent was removed under vacuum, and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to give 209-4 (24 g, 80% yield) which was used without further purification. 1H NMR (400 MHz, DMSO): 6.550 (s, 1H); 7.039 (dd, J=5.2 Hz, J=3.2 Hz, 1H); 7.857 (dd, J=1.6 Hz, J=3.2 Hz, 1H); 8.155 (q, J=1.6 Hz, 1H); 12.418 (br, 1H)

Statistics shows that 1198416-32-8 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; INTERMUNE, INC.; US2009/318455; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1000025-07-9, Adding some certain compound to certain chemical reactions, such as: 1000025-07-9, name is Vadadustat,molecular formula is C14H11ClN2O4, 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 1000025-07-9.

Vadadustat (1 .0g), D-Proline (0.71 g) and methanol (16mL) were charged in a RBF at 25±5C and the contents were heated to 60-65C and stirred for 30-40 minutes at 60-65C. The reaction mass was slowly cooled to 25±5C and maintained under stirring at 25±5C for 16 hours. The product obtained was filtered, washed with prechilled methanol (1 mL) and dried under vacuum for 16 hours at 40C. The solid obtained was identified as 1 :1 co-crystal of Vadadustat D-Proline. Yield: 0.86g.

According to the analysis of related databases, 1000025-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; PILLI, Narasimha Murty; PATHURI, Srinivasarao; GOLIVI, Ramamohana Rao; JAYACHANDRA, Sureshbabu; (36 pag.)WO2020/75199; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem