Tag: M.W:100-200

Synthetic Route of 720666-45-5, 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.720666-45-5, name is 2-Chloro-5-methoxypyridin-3-amine, molecular formula is C6H7ClN2O, molecular weight is 158.5856, as common compound, the synthetic route is as follows.

Example 1 4-(2-CHLORO-5-METHOXYPYRIDIN-3-YLAMINO)-3-CYANO-6-METHOXY- 7- (3-morpholinopropoxy) quinoline Sodium hexamethyldisilazane (1M solution in THF ; 0.76 ml) was added dropwise to a mixture of 3-AMINO-2-CHLORO-5-METHOXYPYRIDINE (0.05 g), 4-chloro-3-cyano- 6-METHOXY-7- (3-MORPHOLINOPROPOXY) quinoline (J. Med. CHEM., 2001,44, 3965-3977 & US Patent No. 6,002, 008; 0.125 g), DMF (2 ml) and THF (5 ml) that had been cooled to 0 C. The mixture was stirred at 0 C for 5 minutes and at ambient temperature for 1 hour. Acetic acid (0.052 ml) was added and the resultant mixture was concentrated by the evaporation of the THF. Solid material was removed by filtration and washed with DMF (2 ml). The resultant concentrate and DMF washings were combined and injected directly on to a Waters Symmetry column (CIS reversed-phase, 5 microns, 19 mm diameter, 100 mm length) and eluted with decreasingly polar mixtures of water (containing 5% methanol and 1% acetic acid) and acetonitrile. The material so obtained was mixed with methylene chloride (20 ml) that contained 5% methanol. Potassium carbonate (0.5 g) was added and the mixture was stirred at ambient temperature for 10 minutes. The solids were filtered off and the filtrate was evaporated. The resultant residue was triturated under diethyl ether. There was thus obtained the title compound as a solid (0.099 g); NMR Spectrum: (CDC13) 2.13 (m, 2H), 2.48 (m, 4H), 2.57 (t, 2H), 3.73 (m, 4H), 3.74 (s, 3H), 3.81 (s, 3H), 4.29 (t, 2H), 6.58 (s, 1H), 6.73 (br s, 1H), 6.9 (s, 1H), 7.48 (s, 1H), 7.81 (s, 1H), 8.78 (s, 1H); Mass Spectrum: M+HS 484 and 486. The 3-AMINO-2-CHLORO-5-METHOXYPYRIDINE used as a starting material were prepared as follows:- A solution of hydrogen peroxide (30% aqueous solution; 4.6 ml) in water (5 ml) was added dropwise (approximately 0.05 ml/minute) to a solution of 3-AMINO-5-METHOXYPYRIDINE (Y. Tamura et AL., J. Org. Chem. , 1981,46, 3564; 3.8 g) in 12N aqueous hydrochloric acid (60 ml) that was heated to 70 C and the resultant mixture was stirred and heated to 70 C for 30 minutes. The mixture was cooled to ambient temperature and the precipitate was isolated. The solid so obtained was 3-amino-2,6-dichloro-5-methoxypyridine (0.165 g). The filtrate was cooled to 0 C and the acidity of the solution was reduced to pH4 by the addition of ION aqueous potassium hydroxide solution. The resultant solution was extracted with methylene chloride and the organic layer was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 4: 1 mixture of petroleum ether (b. p. 40-60 C) and diethyl ether as eluent. There was thus obtained 3-amino- 2-chloro-5-methoxypyridine as a white solid (1.3 g); NMR Spectrum: (CDC13) 3.81 (s, 3H), 4.08 (m, 2H), 6.6 (s, 1H), 7.51 (s, 1H) ; Mass Spectrum: M+H 159. On further elution using a 2: 1 mixture of petroleum ether (b. p. 40-60 C) and diethyl ether, there was obtained as a solid a second portion (0.342 g) of 3-amino-2,6-dichloro-5-methoxypyridine ; NMR Spectrum: (CDC13) 3.86 (s, 3H), 4.12 (m, 2H), 6.65 (s, 1H) ; Mass Spectrum: M+H+ 193.

The chemical industry reduces the impact on the environment during synthesis 720666-45-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/69827; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16063-69-7, 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 16063-69-7 as follows.

2,4,6-Trichloropyridine (20.0 g, 190.63 mmol) was dissolved ethanol (100 mL). Methyl amine (33% wt in ethanol, 81.9 mL, 657 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2 weeks. The white precipitate was filtered off and washed with te/t-butylmethylester and water to give (2,6-dichloro- pyhdin-4-yl)-methylamine (11.9 g, 61 %) as a white crystalline compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16063-69-7, its application will become more common.

Reference:
Patent; NeuroSearch A/S; WO2008/92942; (2008); A2;,
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.10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H8N2, molecular weight is 120.15, as common compound, the synthetic route is as follows.Recommanded Product: 10592-27-5

Step 2; A solution of Br2 (2.78 ml, 8.64 g, 54 mmole) in dry dichloromethane (40 ml) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-10C) solution of 2.3-dihydro-1H-pyrrolo[2,3-b]pyridine (6.5 g,54 mmole) in a mixture of dry dichloromethane (60 ml) and pyridine (6 ml). The suspension was stirred at 0C for 2 hrs, poured into a mixture of NaHCO3 (120 ml) and saturated aqueous Na2S2O3 (15 ml) and extracted with a solution of ethyl acetate/methanol (3X200 ml). The organic layers were concentrated to afford 3.7 g of 5-bromo- 2,3-dihydro- 1H-pyrrolo[2,3-b]pyridine (2) after purification by flash chromatography using dichloromethane as eluent (35% yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.98 ( t, J = 8.54 Hz, 2H ) 3.48 (t, J=8.55 Hz, 2H) 6.58 (bs, 1 H) 7.37(s,1 H) 7.71 (s,1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; EP2070928; (2009); 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.603310-75-4, name is 5-Isopropylpyridin-2-amine, molecular formula is C8H12N2, molecular weight is 136.1943, as common compound, the synthetic route is as follows.Quality Control of 5-Isopropylpyridin-2-amine

General procedure: To the solution of Acid SM-IX (750 mg, 2.i8 mmol, iOO mol-%) in dry DCM (iO ml) under nitrogen atmosphere was added 3-amino-5- methylisoxazole (427 mg, 4.36 mmol, 200 mol-%) and pyridine (526 p1, 6.53mmol, 300 mol-%). T3P (50 w-% in EtOAc) (2.6 ml, 4.36 mmol, 200 mol-%) was added dropwise and the reaction mixture stirred at rt for four hours. DCM (i 0 ml) and i 0 % NaH 003 (30 ml) were added. The water phase was extracted twice with DCM (2 x iO ml). The organic phases were combined and washed with 0.i N HCI solution (3 x 30 ml), water (3 x 30 ml) and finally withbrine (3 x 30 ml) and dried with sodium sulfate. The crude yield of compound i was 95 % (875 mg).1H NMR (200 MHz, DMSO-d6): 0.97 (5, 3 H), i.24 -2.46 (m, i6 H),2.37 (5, 3H), 2.58 – 3.Oi (m, 2 H), 6.64 (5, i H), 6.88-7.06 (m, i H), 7.07 – 7.25 (m, 2 H), iO.88 (5, i H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,603310-75-4, 5-Isopropylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; FORENDO PHARMA LTD; HIRVELAe, Leena; HAKOLA, Marjo; LINNANEN, Tero; KOSKIMIES, Pasi; STJERNSCHANTZ, Camilla; (182 pag.)WO2018/224736; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-81-3, 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. 113118-81-3, name is 5-Bromonicotinaldehyde. A new synthetic method of this compound is introduced below.

INTERMEDIATE 75 PREPARATION OF 5-FORMYLPYRIDINE-3-CARBONITRILE A mixture of of 5-bromopyridine-3-carbaldehyde (10 g, 53.8 mmol) and cuprous cyanide (7.20 g, 80.6 mmol) in N,N-dimethylformamide (40 mL) was heated to 140 FontWeight=”Bold” FontSize=”10″ C and stirred under a nitrogen atmosphere overnight. After being cooled to room temperature, the reaction mixture was diluted with water (80 mL) and filtered. The filtrate was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (EtOAc-petroleum ether, 1:4) to afford the title compound (1.86 g, 26%) as a yellow solid.1H NMR (400 MHz, CDCl3) delta 10.17 (s, 1H), 9.30 (s, 1H), 9.14 (s, 1H), 8.45 (t, J = 2.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; DENALI THERAPEUTICS INC.; BONANOMI, Giorgio; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; LESLIE, Colin Philip; LYSSIKATOS, Joseph P.; NAPOLITANO, Carmela; POZZAN, Alfonso; SUDHAKAR, Anantha; SWEENEY, Zachary K.; TONELLI, Federica; DE VICENTE FIDALGO, Javier; (232 pag.)WO2017/96301; (2017); 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. 144100-07-2, name is 2-Bromo-6-fluoropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-6-fluoropyridine

A mixture of 2-bromo-6-fluoropyridine (352mg, 2mmol), tert-butyl- 1 ,4-di azepane- 1- carboxylate (400mg, 2mmol), Pd2(dba)3 (91.5mg, 0.lmmol), BINAP (124.4mg, 0.2mmol), and tBuONa (3 84mg, 4mmol) in toluene (20 ml) was stirred at 80 C for 3h under N2 atmosphere. The mixture was then purified by chromatography (silica, PE/EtOAc = 5:1) to afford tert-butyl-4-(6- methylpyridin-2-yl)-1,4-diazepane-1-carboxylate (400mg, 1.3Smmol, 68%) as yellow oil. ESIMS (EI+, m/z): 296.1 [M+H]t

The synthetic route of 144100-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; O’NEILL, David John; SAIAH, Eddine; KANG, Seong Woo Anthony; BREARLEY, Andrew; BENTLEY, Jonathan; (565 pag.)WO2018/89433; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 100-48-1, Isonicotinonitrile, 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 C6H4N2, blongs to pyridine-derivatives compound. Computed Properties of C6H4N2

General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL). N’-Hydroxyisonicotinimidamide (AM-1). Compound was synthesized by following GP1 starting from isonicotinonitrile (10 g, 0.1 mol) in 85% (11.6 g) yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-48-1, Isonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Article; Geyl, Kirill; Baykov, Sergey; Tarasenko, Marina; Zelenkov, Lev E.; Matveevskaya, Vladislava; Boyarskiy, Vadim P.; Tetrahedron Letters; vol. 60; 40; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72830-08-1, 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. 72830-08-1, name is (3,4-Dimethoxypyridin-2-yl)methanol, molecular formula is C8H11NO3, 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.

Add 9.22 kg of toluene,Add at room temperature2-hydroxymethyl-3,4-dimethoxypyridine 1.5kg,Cool down to 3 C ~ 10 C,Add 1.63 kg of thionyl chloride within 1 to 2 hours at 3 to 10 C.After the addition, the mixture was stirred at 5 to 10 C for 1 hour.Increase the temperature to 35 C ~ 40 C within 1 hour,Incubate at 35-40 C for 4 hours.After TLC detection, the temperature control is 35-40 C.Vacuum distilling thionyl chloride for 3 to 4 hours, adding 9 kg of toluene, and cooling to 20 to 25 C.Centrifugal filtration, 0.64 L of toluene washed filter cake, drained,Drying at 50-55 C for 6-8 hours,2-Chloromethyl-3,4-dimethoxypyridine hydrochloride (III) was obtained.

According to the analysis of related databases, 72830-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Tiantaishan Pharmaceutical Co., Ltd.; Wang Jing; Jiang Wei; Xie Xiaofei; Zeng Yehao; Wang Wei; Gong Shiyu; Zhao Dongming; (29 pag.)CN109354587; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 626-55-1, 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. 626-55-1, name is 3-Bromopyridine, molecular formula is C5H4BrN, 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.

Under an N2 atmosphere, a 1.6 M solution of n-butyllithium inhexane (7.06 mL, 11.3 mmol) was added slowly to a cooled(78 C) solution of diisopropylamine (1.25 g, 1.73 mL, 12.4 mmol)in THF (25 mL). After 30-min stirring at 0 C, the mixture wascooled to 78 C and a solution of 3-bromopyridine (5, 1.63 g,1.00 mL, 10.3 mmol) in THF (5 mmol) was added slowly. The mixturewas stirred at 78 C for 15 min, and then a solution ofN-formylpiperidine (5.24 g, 5.14 mL, 46.4 mmol) was addedslowly. The solution was stirred at 78 C for 50 min. Then itwas allowed to warm to room temperature and stirred for another1.5 h. Saturated NH4Cl solution (40 mL) was added. The aqueouslayer was extracted with EtOAc (3 30 mL). The combined organiclayers were washed with brine (60 mL) and dried over Na2SO4.Filtration and evaporation afforded crude product, which waspurified by fc (5.5 cm, EtOAc/cyclohexane 1:4). Yellow solid(EtOAc/cyclohexane2:1, Rf = 0.55), yield 914 mg (48%). 1H NMR(600 MHz, CDCl3): d (ppm) = 7.22 (d, J = 4.9 Hz, 1H, 5-H-Py), 8.72(d, J = 4.9 Hz, 1H, 6-H-Py), 8.92 (s, 1H, 2-H-Py), 10.37 (s, 1H, CHO).

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 626-55-1, 3-Bromopyridine.

Reference:
Article; Miyata, Kengo; Moeller, Guido; Schepmann, Dirk; Wuensch, Bernhard; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4277 – 4284;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7598-35-8, Adding some certain compound to certain chemical reactions, such as: 7598-35-8, name is 2-Bromopyridin-4-amine,molecular formula is C5H5BrN2, 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 7598-35-8.

Example 5N-(4-{[l-(4-fluoropyridin-2-yl)-lH-indol-5-yl]oxy}pyrimidin-2-yl)benzene-l,3-diamine (Compound 76)For the preparation of Compound 77, 2-bromo-4-fluoropyridine was prepared utilizing a modified procedure described in the reference below, and used in the indole arylation reaction. Thibault, C; L’etaeureux, A.; Bhide, R. S.; Ruel, R. Org. Lett. 2003, 5, 5023-5025.Step 1: 2-bromo-4-fluoropyridine.To a stirred suspension of 2-bromopyridin-4-amine (0.50 g, 2.9 mMol) in 50% aqueous HBF4 (6.0 mL) was added a solution of sodium nitrite (0.24 g, 3.5 mMol) in water (3.0 mL) over 5 minutes at 0 0C. The resulting mixture was allowed to warm to ambient, and was stirred for 12 hours. Solid NaHCO3 was added slowly, until CO2 evolution ceased, and the resulting aqueous solution was extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with saturated NaHCO3 (1 x 30 mL), and brine (1 x 30 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to afford the title compound.

According to the analysis of related databases, 7598-35-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2007/35309; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem