Tag: M.W:200-300

Reference of 72830-09-2, 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride. A new synthetic method of this compound is introduced below.

Examples; Starting compounds and intermediates; 2-(3,4-Dimethoxy-pyridine-2-ylmethylsulfanyl)-5-methoxy-3H-imidazo[4,5-b]pyridine A reaction mixture of 10.00 g (55.20 mmol) 5-methoxy-3H-imidazo[4,5-b]pyridine-2-thiol and 12.37 g (55.20 mmol) 2-chloromethyl-3,4-dimethoxy pyridinium chloride in isopropanol (200 ml) is stirred for 2 h under reflux. The mixture is concentrated, filtered and dried at 60C for 16 h. Afterwards the crude hydrochloride of the product is suspended in a mixture of water dichloromethane and is basified to pH 8 by adding sodium hydroxide solution (6 N). The mixture is extracted with dichloromethane three times. The combined organic layers are washed with water, dried over calcium chloride, concentrated in vacuo, reslurried in acetone and dried again in vacuo to give 14.76 g (44.4 mmol / 80 %) of the title product with a melting point of 157.0C (acetone).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride, and friends who are interested can also refer to it.

Reference:
Patent; ALTANA PHARMA AG; WO2005/105799; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-14-0 , The common heterocyclic compound, 1083057-14-0, name is tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate, molecular formula is C17H20N2O2, 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.

Synthesis of 3-(6-(l-(2,2-difluorobenzo[d] [l,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)-t-butylbenzoate (compound 8).[00265] Compound 7 is dissolved in toluene (2.5 vol based on acid chloride) and added via addition funnel to a mixture of compound 6 (1 eq), dimethylaminopyridine (DMAP, 0.02 eq), and triethylamine (3.0 eq) in toluene (4 vol based on compound 6). After 2 hours, water (4 vol based on compound 6) is added to the reaction mixture. After stirring for 30 minutes, the layers are separated. The organic phase is then filtered and concentrated to afford a thick oil of compound 8 (quantitative crude yield). MeCN (3 vol based on crude product) is added and distilled until crystallization occurs. Water (2 vol based on crude product) is added and the mixture stirred for 2 h. The solid is collected by filtration, washed with 1 : 1 (by volume) MeCN/water (2 x 1 vol based on crude product), and partially dried on the filter under vacuum. The solid is dried to constant weight (<1% difference) in a vacuum oven at 60 0C with a slight N2 bleed to afford 3-(6-(l-(2,2-difluorobenzo[d][l,3]dioxol-5-yl) cyclopropanecarboxamido)-3- methylpyridin-2-yl)-t-butylbenzoate as a brown solid. The synthetic route of 1083057-14-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/76142; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79456-30-7 ,Some common heterocyclic compound, 79456-30-7, molecular formula is C6H4BrF3N2, 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.

Production Example 59-2 40 g of 3-bromo-5-trifluoromethyl-pyridin-2-ylamine, 2.2 g of copper (II) acetylacetone, 6.6 g of acetylacetone, 59 g cf cesium carbonate, and 105 mL of NMP were added to an autoclave reactor, and 25 mL of a 28% ammonia water solution was added thereto under ice-cooling. After sealing the reactor, the temperature was elevated to 110C and the mixture was heated and stirred for 12 hours. After ice-cooling to room temperature, the reaction mixture was diluted with water and was subjected to extraction using ethyl acetate. A combined organic layer was dried using sodium sulfate, and then, was condensed under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 15 g of 5-trifluoromethyl-pyridine-2,3-diamine. 5-trifluoromethyl-pyridine-2,3-diamine 1H-NMR (CDC13) delta: 7.93 (1H, d), 7.04 (1H, d), 4.71 (2H, brs), 3.46 (2H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,79456-30-7, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; SUZUKI, Tatsuya; IWATA, Atsushi; NOKURA, Yoshihiko; EP2865266; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, molecular weight is 281.89, as common compound, the synthetic route is as follows.Computed Properties of C5H2Br2N2O2

To a stirred solution of 2,5-dibromo-3-nitropyridine (226 mg, 0.802 mmol), (4- (1 ,4-dimethyl- 1H- 1 ,2,3-triazol-5-yl)-3-fluorophenyl)boronic acid (282.6 mg, 1.20 mmol),and PdC12(dppf) (29.3 mg, 0.040 mmol) in THF (8.0 mL) was added tripotassium phosphate (3M in H20, 802 pi, 2.41 mmol), purged with N2 (vacuum/N2 x3) and the reaction was heated at 75 C with stirring for 1 h. The reaction was cooled to room temperature and concentrated. The residue was suspended in EtOAc, filtered throughCelite, washed with EtOAc, concentrated. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0% to 100% using solvent A/B=CH2C12/EtOAc over 15 column volumes, RediSep Si02 40 g, loaded as DCM solution). Obtained the product (190 mg, 61%): HPLC: RT=0.91 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.1%TFA, 1.5 mm gradient,wavelength=254nm); MS (ES): m/z=392 [M+1f

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-37-0, 2,5-Dibromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885277-08-7, Adding some certain compound to certain chemical reactions, such as: 885277-08-7, name is 5-Chloropyridine-2-sulfonyl chloride,molecular formula is C5H3Cl2NO2S, 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 885277-08-7.

To a solution of Example 3B (60.0 mg, 0.187 mmol) and 5-chloropyridine-2-sulfonyl chloride (43.6 mg, 0.205 mmol) in N,N-dimethylformamide (1.5 mL) was added triethylamine (0.065 mL, 0.467 mmol). The mixture was stirred for 2 hours, quenched with saturated NaHC( and brine, and extracted with ethyl acetate (2x). The combined organic layers were concentrated, and the residue was purified by reverse-phase HPLC (see protocol in Example 273E) to provide the title compound (26.7 mg, 31 %). JH NMR (500 MHz, DMSO-<) delta ppm 9.05 (s, 1H), 8.85 (dd, J = 2.5, 0.7 Hz, 1H), 8.65 (s, 1H), 8.24 (dd, J = 8.4, 2.4 Hz, 1H), 8.00 (dd, J = 8.4, 0.7 Hz, 1H), 7.48 (t, J = 8.8 Hz, 1H), 7.03 (dd, J = 11.3, 2.9 Hz, 1H), 6.81 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.42 (s, 2H), 1.96 (s, 6H); MS (ESI+) m/z 460.3 (M+H)+. 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. 885277-08-7, 5-Chloropyridine-2-sulfonyl chloride, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 117007-52-0, 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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below.

Step 3: tert-butyl 3-iodo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (49-4); A magnetically stirred suspension of 1.20 g (4.90 mmol) of 3-iodo-1H-pyrazolo[3,4-b]pyridine (49-3) in 35 mL of anhydrous acetonitrile under a nitrogen atmosphere was treated with 720 muL (5.15 mmol) of triethylamine, followed by 599 mg (4.90 mmol) of 4-dimethylaminopyridine. The resulting solution was treated approximately 2 minutes later with a solution of 1.29 g (5.88 mmol) of BOC anhydride in 5 mL of anhydrous acetonitrile, and the resulting solution stirred at room temperature for 72 hours. The crude reaction mixture was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine, and dried in vacuo (anhydrous MgSO4). The dried extract was filtered, and the filtrate concentrated in vacuo to give 2 g of the crude solid product. The product was purified by flash chromatography over silica gel with 20:1 hexanes/EtoAc (crude material dissolved in chloroform, impregnated on silica, and the silica applied to the top of the column) to give the desired product as a white solid. M+=245 (M-100, loss of BOC). 1H NMR (CDCl3): 1.73(s, 9H), 7.36(dq, 1H), 7.84(dd,1H), 7.78(dd,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Saggar, Sandeep A.; Sisko, John T.; Tucker, Thomas J.; Tynebor, Robert M.; Su, Dai-Shi; Anthony, Neville J.; US2007/21442; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 66572-56-3, 2-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, Formula: C6H4BrNO2, blongs to pyridine-derivatives compound. Formula: C6H4BrNO2

a) 2-Bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide To a stirred solution of 455 mg (2.25 mmol) 2-bromo-isonicotinic acid in 8 ml THF were added 914 mg (2.40 mmol) HATU and 0.50 ml (4.51 mmol) N-methylmorpholine and stirring continued at 50 C. for 16 h. 200 mg (0.75 mmol) 7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine was then added and stirring continued at 60 C. for 4 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (methanol/dichloromethane) afforded 208 mg (62%) 2-bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide as a yellow crystalline solid. ES-MS m/e (%): 452 (M{81Br}+H+, 95), 450 (M{79Br}+H+, 100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66572-56-3, 2-Bromoisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Norcross, Roger David; US2005/65151; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 200064-11-5, 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. 200064-11-5, name is 4-(5-Bromo-2-pyridyl)morpholine. A new synthetic method of this compound is introduced below.

Under the protection of nitrogen, CuI (1 mmol), Cs2CO3 (20 mmol) and ethyl 2-oxocyclohexylcarboxylate (2 mmol) were added to DMSO (10 mL).Stir at room temperature for 30 min.5-hydroxy-3-methoxy-4-phenylquinolin-2(1H)-one (10 mmol) and 4-(5-bromopyridin-2-yl)morpholine (10 mmol) in DMSO (12 mL) solution, added by injection.Heat to 100 C overnight. Cool to room temperature, filter, add water (50 mL) and dichloromethane (50 mL×3) and collect organics.The solvent was evaporated under reduced pressure, and the crude material was purified by column chromatography to give 5-hydroxy-3-methoxy-1-(6-morpholinylpyridin-3-yl)-4-phenylquinolin-2 (1H) -ketone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,200064-11-5, its application will become more common.

Reference:
Patent; Ocean University of China; Shao Changlun; (69 pag.)CN108658937; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.930093-72-4, name is 4-Chloro-5-methyl-6-((2-methylpyridin-3-yl)oxy)pyrimidine, molecular formula is C11H10ClN3O, molecular weight is 235.6696, as common compound, the synthetic route is as follows.category: pyridine-derivatives

A solution of KOBut (2.4 mL, 1.0 M in THF, 2.34 mmol) was added to a solution of alcohol 50B (0.42 g, 1.95 mmol) and the chloride IB (0.56 g, 2.39 mmol) in anhydrous THF (10 mL) under nitrogen at 0 C and stirred at 0 C to room temperature for 16 hours. The reaction was quenched with saturated NH4Cl solution (15 mL) and extracted with EtOAc (30 mL * 3). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified on a silica gel column (ISCO) with MeOH (NiH3) in dichloromethane (0-»5%) to provide compound 158 (0.81 g, 99% yield). LCMS: 416.5

At the same time, in my other blogs, there are other synthetic methods of this type of compound,930093-72-4, 4-Chloro-5-methyl-6-((2-methylpyridin-3-yl)oxy)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 15862-37-0, 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.15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, molecular weight is 281.89, as common compound, the synthetic route is as follows.

In a 250 mL thick-walled flask was added (2-chloropyrimidin-5-yl)boronic acid (1 g, 6.32 mmol),2,5-dibromo-3-nitropyridine (1.780 g, 6.32 mmol) in 90 mL of THF. Added tripotassium phosphate (2.68 g, 12.6 mmol)and PdChidppO-CLhChAdduct (0.103 g, 0.126 mmol) . Bubbled in argon through the mixture while sonicating for 1 min. Capped flask and heated in an oil bath at 65 C overnight. Concentrated to afford a brown solid. The crude material was purified on a 120 g ISCO column, eluting with 20% EtOAc/hexanes to 50% EtOAc/hexanes over 20 column volumes. The fractions containing the title compound were concentrated to afford 0.72 g (36% yield) of a yellow solid. NMR (400MHz, CDCh) delta 9.04 (d, J=2.0 Hz, 1H), 8.83 (s, 2H), 8.58 (d, J=2.0 Hz, 1H).

Statistics shows that 15862-37-0 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromo-3-nitropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem