Tag: M.W:200-300

Reference of 96166-00-6 ,Some common heterocyclic compound, 96166-00-6, molecular formula is C12H12N2O, 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 toluene solution (331 g) of the obtained 2-amino-5-benzyloxypyridine,Ethanol (217 g) and 10% Pd / C (2.28 g, moisture content 53%) were charged in an autoclave and reacted at 25 C. for 4 hours while being introduced at 0.2 MPa (absolute pressure) in a hydrogen atmosphere.After completion of the reaction, Pd / C was filtered and the residue was washed with ethanol (76 g).The filtrate was dried under reduced pressure to obtain 2-amino-5-hydroxypyridine (25.6 g, 0.23 mol) (yield 92%).

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. 96166-00-6, 5-(Benzyloxy)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KOEI CHEMICAL COMPANY LIMITED; TAKAHASHI, SATOSHI; NIHEI, YURI; (24 pag.)JP2017/48131; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 941294-57-1, 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.941294-57-1, name is 5-Bromo-2-iodo-4-methylpyridine, molecular formula is C6H5BrIN, molecular weight is 297.92, as common compound, the synthetic route is as follows.

To a suspension of 5-bromo-2-iodo-4-methylpyridine(1g, 3.36 mmol) in NMP (6mL) with an inert atmosphere of argon, KF (0.585 g, 10.07 mmol), Cul (1.92 g, 10.08 mmol) and CF3SiMe3 (2.49 mL, 15.07 mmol) were added. The resulting solution was stirred overnight at 60C. After cooling, the mixture was poured into 12% aqueous ammonia, and then extracted with Et2O. The organic solutions were combined, dried over MgSO4, filtered and concentrated. Purification of the crude residue by normal phase chromatography (0% to 100%, hexane – diethyl ether) afforded the desired product (23% yield) as a yellow oil.

Statistics shows that 941294-57-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-iodo-4-methylpyridine.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Gonzalez Rodriguez, Jacob; Gual Roig, Silvia; Esteve Trias, Cristina; Vidal Gispert, Laura; EP2738172; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887583-90-6, 4-Bromo-2-(trifluoromethyl)pyridine, 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, COA of Formula: C6H3BrF3N, blongs to pyridine-derivatives compound. COA of Formula: C6H3BrF3N

A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 10.6 mL, 13.8 mmol) was added dropwise by syringe to a solution of 4-bromo-2-(trifluoromethyl)pyridine (3.12 g, 13.8 mmol) in dry THF (50 mL) at 0 C. After 30 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.38 g, 12.5 mmol) in THF (28.5 mL) was added to the Grignard solution by syringe at 0 C. The reaction mixture was warmed to room temperature over 2 hours after which it was quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate and washed with saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887583-90-6, 4-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1013648-04-8, Adding some certain compound to certain chemical reactions, such as: 1013648-04-8, name is Methyl 2,6-dichloro-4-methylnicotinate,molecular formula is C8H7Cl2NO2, 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 1013648-04-8.

) Synthesis of 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterA solution of 5.2 g (23.7 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester, 3.94 g (28.5 mmol) K2C03 and 2.06 ml (23.7 mmol) morpholine in DMF (48 ml) was heated to 60 C for 16 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1 ) provided 1.95 g (7.2 mmol, 30%) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

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. 1013648-04-8, Methyl 2,6-dichloro-4-methylnicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); 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.1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate, molecular formula is C7H5BrFNO2, molecular weight is 234.02, as common compound, the synthetic route is as follows.Formula: C7H5BrFNO2

Intermediate 19-5 5-Fluoro-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxylic acid (1369) (1370) 500 mg of methyl 6-bromo-5-fluoropyridine-2-carboxylate were reacted analogously with 533 mg (1.2 equiv.) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole in the microwave at 120 C. for 90 min. This gave 380 mg (80% of theory) of the title compound as a crude product. (1371) UPLC-MS (Method A1): Rt=0.72 min (1372) MS (ESIpos): m/z=222 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1210419-26-3, Methyl 6-bromo-5-fluoropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BOTHE, Ulrich; SIEBENEICHER, Holger; SCHMIDT, Nicole; ROTGERI, Andrea; BOeMER, Ulf; RING, Sven; IRLBACHER, Horst; GUeNTHER, Judith; STEUBER, Holger; LANGE, Martin; SCHAeFER, Martina; (191 pag.)US2016/311833; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 889676-37-3 ,Some common heterocyclic compound, 889676-37-3, molecular formula is C6H5BrN2O, 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 1-11: tert-Butyl 6-r5-carbamoylpyridin-2-ylV4-oxospirorchroman-2,4′-pirhoeridmel-r-carboxylatel’-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)spiro[chroman-2,4′-piperidm]-4-one (40.0 g, 90.0 mmol), 6-chloronicotinamide (17.0 g, 108 mmol), Pd(PPh3)4 (5.21 g, 4.51 mmol), and aqueous 2M Na2CO3 (100 ml) solution were suspended in dioxane (300 ml) and heated at 100C for 16 h. The reaction mixture was diluted with CEtaCI3 and H2O, the aqueous layer was extracted with CHCI3. The combined organic layer was washed with brine, dried over MgSCvj. and silicagel. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by crystallization (CHCI3 -EtOAc) to obtain the intended compound as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,889676-37-3, its application will become more common.

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; JONA, Hideki; SHIBATA, Yoshihiro; YAMAKAWA, Takeru; WO2010/2010; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884494-49-9, 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.884494-49-9, name is 2-Chloro-5-fluoro-4-iodopyridine, molecular formula is C5H2ClFIN, molecular weight is 257.432, as common compound, the synthetic route is as follows.

A batch with 2-chloro-5-fluoro-4-iodopyridine [CAS-RN: 884494-49-9] (3000 mg; 11.65 mmol), (4- fluoro-3-methoxyphenyl)boronic acid [CAS-RN: 854778-31-7] (1981 mg; 11.65 mmol) and [1,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II) [CAS-RN: 72287-26-4] (952 mg; 1.17 mmol) in 1 ,2-dimethoxyethane (30.0 mL) and 2 M aqueous solution of potassium carbonate (23 mL) was degassed using argon. The batch was stirred under an atmosphere of argon for 4 hours at 100 C. After cooling, the batch was diluted with ethyl acetate and THF and washed with a saturated aqueous solution of sodium chloride. The organic layer was filtered using a Whatman filter and concentrated. The residue was purified by column chromatography (hexane to hexane / ethyl acetate 50%) to give the title compound (2600 mg; 10.2 mmol). ‘H-NMR (400MHZ, DMSO-de): delta [ppm]= 3.92 (s, 3H), 7.28 (ddt, 1H), 7.39 (dd, 1H), 7.48 (dd, 1H), 7.86 (d, 1H), 8.55 (d, 1H).

Statistics shows that 884494-49-9 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-fluoro-4-iodopyridine.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; LUeCKING, Ulrich; HOG, Daniel; CHRIST, Clara; SACK, Ulrike; SIEGEL, Franziska; LIENAU, Philip; WERBECK, Nicolas; (195 pag.)WO2018/177899; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63897-12-1, 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. 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 3 3-Amino-2,4-bis(methylthio)-6-methylpyridine To a solution of 15.5 g (0.22 mol) sodium methanethiolate in 200 ml methanol was added slowly with stirring under nitrogen a solution of 20.8 g (0.1 mol) 3-nitro-2,4-dichloro-6-methylpyridine in 150 ml methanol. A precipitate formed and the mixture was stirred overnight at room temperature. The mixture was then filtered and the solid was washed first with methanol and then with water. 3-Nitro-2,4-bis(methylthio)-6-methylpyridine (18.9 g, 82% yield) was obtained as a yellow solid, mp 172-176C. 1 H NMR (CDCl3): delta2.45 (s, 3H); 2.51 (s, 3H); 2.55 (s, 3H); 6.77 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63897-12-1, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5596001; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211533-83-3, 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. 1211533-83-3, name is 5-Bromo-6-methoxypyridin-2-amine, molecular formula is C6H7BrN2O, 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.

To a solution of 5-bromo-6-methoxypyridin-2-amine (1.0 g, 4.9 mmol) in DCM (20.0 mL) was added 2-methylbenzenesulfonyl chloride (1.1 g, 5.9 mmol, 853.6 uL) and pyridine (1.2 g, 14.8 mmol, 1.2 mL). The mixture was stirred at 45C for 12 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (S1O2, Petroleum ether / Ethyl acetate = 100/1 to 50/1) to afford N-(5-bromo-6-methoxypyridin- 2-yl)-2-methylbenzenesulfonamide (1.0 g, 2.5 mmol, 52.2% yield). M+H+ = 357.0 (LCMS).

According to the analysis of related databases, 1211533-83-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (214 pag.)WO2019/94641; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, molecular formula is C12H11ClN2O, 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.

Following hydrogenation to form the first aniline intermediate, acid catalyzed coupling was performed to prepare 4-[3-chloro-4-(2-pyridylmethoxy)anilino]-3-cyano-7-ethoxy-6-N-acetylaminoquinoline, as shown below: To perform the coupling reaction, the two reactants were heated together in alcohol at 65-78 C. over 4-6 hours, yielding the product. The reaction begins as an amber slurry and thickens to a lighter beige slurry as it approaches completion. Upon scaling up from 75 g to 350 g, it proved necessary to add a catalytic amount (0.025 eq.) of methanesulfonic acid to initiate the reaction. As a specific example, 4-chloro-3-cyano-7-ethoxy-6-N-acetylaminoquinoline (0.141 kg, 0.49 mole) was added to the mixture of Example 2, followed by ethanol (0.037 L) to give a suspension. A catalytic amount of methanesulfonic acid (1.17 g) was added at 20-25 C. The resulting slurry was heated to 70-75 C. and held for a minimum of 4 hours. Thickening of the slurry was evident after 1.5 hours. Following reaction completion, the mixture was cooled to room temperature and may be used ?as is? in the telescoped reaction of Example 4 below.; As solvents EtOH, DMF or other suitable solvent may be used. Experimental results obtained using different solvents and reaction conditions are shown in Table 3. Difficulty filtering the product of this step (noted in several entries on Table 3) was circumvented by not isolating the solid at this point, but telescoping the reaction with the next step. It has been found that on the order of 20 volumes of EtOH were necessary to achieve reasonable stirring, but that the reaction can proceed in only 10 volumes of DMF, without significant loss in purity. In Table 3, where the entry is labelled NI, the intermediate product was not isolated, but carried into the next reaction step. TABLE 3 Coupling Reaction Coupling Temp Time Yield Solvent Solvent ( C.) (h) (%) Comments IPA EtOH 78 4 85.4 contains impurity THF EtOH 78 4 90.5 v. slow filtration THF THF 68 4 NA Only 16% product formed THF EtOH 78 4 94.2 v. slow filtration EtOH IPA 82 5 NA No reaction EtOH MeOH 65 5 60.0 v. slow filtration THF EtOH 78 1.5 80.3 v. slow filtration (MeSO3H) THF EtOH 78 4 86.0 v. slow filtration THF EtOH 78 3 85.7 4 h filtration – hard, green (MeSO3H) coated solid on drying THF Dimethoxy 85 2 74.2 Faster filtration (<1 hr) ethane Nice yellow solid THF Diethoxy 85 5 - - Methane THF Dimethoxy 70 6 - - Ethane THF EtOH 78 6 96.6 Slow filtration THF DMF 78 0.5 65.6 Some product lost in filtrate (MeSO3H) THF DMF 70 8 NI See Note 1 (MeSO3H) THF EtOH 78 6 ND See Note 2 (MeSO3H) THF EtOH 78 4 NI Yield to the free base is (MeSO3H) 80.4%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 83%3/ THF EtOH 75 4 NI Yield to the free base is (MeSO3H) 86%3/ NR = no reaction, NI = not isolated; ND = not determined; NA = not available 1. Carried through to the deprotection and generation of free base to give 69.5% overall yield. 2. The overall yield after the deprotection and generation of the free base is 76.1% 3This reaction was not filtered at all but taken as slurry to the next step. 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 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem