Day: March 9, 2021

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. 1104455-41-5, name is Methyl 4-chloro-5-methylpicolinate. A new synthetic method of this compound is introduced below., Product Details of 1104455-41-5

A mixture of methyl 4-chloro-5-methylpyridine-2-carboxylate (200 mg, 1.08 mmol), 1- cyclopropyl-4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (302.7 mg, 1.29 mmol), Pd(dppf)Cl2-CH2Cl2 (88.0 mg, 0.11 mmol), and K2CO3 (446.8 mg, 3.23 mmol) in dioxane (4 mL) and water (1 mL) was stirred at 80 C for 2 h under nitrogen atmosphere. After cooling to room temperature, the residue was purified by reverse phase flash 33 chromatography with 40-70% MeCN in H2O to afford compound l3-a (60 mg, 21.64%) as a yellow solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1104455-41-5, Methyl 4-chloro-5-methylpicolinate.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WANG, Guoqiang; SHEN, Ruichao; GRANGER, Brett; HE, Jing; XING, Xuechao; HE, Yong; LONG, Jiang; MA, Jun; WANG, Bin; OR, Yat, Sun; (99 pag.)WO2019/213244; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 101990-73-2, name is 2-Chloro-4-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, 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. Recommanded Product: 2-Chloro-4-(chloromethyl)pyridine

To a solution of 6-methyl-3-(5-(4-(trifluoromethoxy)phenyl)-l,3,4-oxadiazol-2- yl)pyridin-2(lH)-one (177 mg, 0.52 mmol) in DMF (10 mL) was added Cs2C03(652 mg, 2.0 mmol), Nal (15 mg, 0.10 mmol) and 2-chloro-4- (chloromethyl)pyridine (172 mu, 1.40 mmol). The reaction mixture was heated at 65 C for 16 hours. The reaction mixture was allowed to cool to RT, brine was added, and the aqueous phase was extraced with EtOAc (3 X 10 mL). The combined organic phases were dried over Na2S04, filtered, and the solvent was evaporated. The residue was purified by Biotage (SNAP 25, 20% to 100% EtOAc in hexanes, followed by 2% to 30%MeOH in DCM) to provide 2-(2-((2-chloropyridin-4- yl)methoxy)-6-methylpyridin-3-yl)-5-(4-(trifluoromethoxy)phenyl)- 1,3,4- oxadiazole (132 mg, 28%), and l-((2-chloropyridin-4-yl)methyl)-6-methyl-3-(5-(4- (trifluoromethoxy)phenyl)-l,3,4-oxadiazol-2-yl)pyridin-2(lH)-one (183 mg, 39%). MS (ES+)2-(2-((2-chloropyridin-4-yl)methoxy)-6-methylpyridin-3-yl)-5-(4- (trifluoromethoxy)phenyl)-l,3,4-oxadiazole C2iHi4QF3N4C>3 requires: 462/464, found: 463/465 [M+H]+; l-((2-chloropyridin-4-yl)methyl)-6-methyl-3-(5-(4- (trifluoromethoxy)phenyl)-l ,3,4-oxadiazol-2-yl)pyridin-2(lH)-one MS (ES+) C2iH14ClF3N403requires: 462, found: 463 [M+H]+; *H NMR (600 MHz, MeOH- d4) (58.36 (d, / = 5.3Hz, 1H), 8.34 (d, / = 7.4 Hz, 1H), 8.19 (d, / = 7.7 Hz, 2H), 7.33 (d, J = 7.7 Hz, 2H),7.26 (s, 1H), 7.05 (d, J = 5.3 Hz,lH),6.35 (d, J = 7.4 Hz,lH),5.42 (s, 2H), 2.31 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 101990-73-2.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; MARSZALEK, Joe; LIU, Gang; KANG, Zhijun; CARROLL, Christopher, L.; MCAFOOS, Timothy; CZAKO, Barbara; WO2014/31928; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55314-16-4 ,Some common heterocyclic compound, 55314-16-4, molecular formula is C10H12N2O, 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.

3-Mercapto-4-methyl-N-(3-(4-methyl-1-1H-imidazole)-5-(trifluoromethyl)phenyl)benzamide was added to the reaction flask.(Intermediate D, 41.6 g, 0.1 mol, 1.0 eq.),3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (starting material SM3, 22.9 g, 0.13 mol, 1.3 eq.),Potassium carbonate (30.4 g, 0.22 mol, 2.2 eq.), N,N-dimethylformamide (320 mL).The reaction temperature is raised to 100 to 110 C for 20 to 30 hours.The reaction was monitored by high performance liquid chromatography, and the temperature was lowered to 0 to 10 C, water (84 g) was added, and the mixture was stirred for 1 to 2 hours.After suction filtration, the obtained solid and water (60 g) were placed in a 100 mL three-neck flask, and kept at 0 to 10 C for 1 to 2 hours.After suction filtration, the obtained solid was washed with water (18 g), and dried under vacuum at 45 to 55 C for 14 to 18 hours to give a crude compound. Add the crude compound E and (450 mL) methanol to a 500 mL reaction flask and heat to 60-65 C.After the solid is dissolved, the temperature is slowly lowered to 0 to 5 C, and the cooling time is controlled for 3 to 4 hours.After that, the mixture was stirred at 0 to 5 C for 3 to 4 hours.Filtration and washing of the solid with ice-methanol (0 – 5 C, 15 g).The solid was collected and dried under reduced pressure at 45 to 55 C for 14 to 18 hours.The target compound nilotinib 46.6 g was obtained as a white solid with a molar yield of 88%.

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. 55314-16-4, 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Fu Xingxing Tai Pharmaceutical Technology Co., Ltd.; Liu Xuejun; Chen Xiaodong; Hao Lu; Wu Feng; (23 pag.)CN109666023; (2019); A;,
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. 13534-97-9, name is 6-Bromopyridin-3-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 13534-97-9

To a stirred solution of 6-bromopyridin-3-amine (2.0 g, 11.56 mmol) in DCM (50 mL), 2-phenylacetic acid (2.04 g, 15.02 mmol), and TEA (4.60 g, 46.24 mmol) were added, followed by the addition of T3P (9.19 g, 28.90 mmol) at 0C. The resulting mixture was stirred at rt for 16 h. The reaction mixture was washed with saturated NaHCOs aqueous solution (100 mL). The organic layer was dried over anhydrous Na2S04 and filtered. The filtered solution was concentrated under reduced pressure and the resulting crude compound was purified by flash column chromatography using 25% ethyl acetate in pet ether as eluent to afford the title compound (2,30 g, 68%) as an off-white solid.LC-MS (method 1): Rt = 2.46 min; m/z = 291.08 (M+H+).

The synthetic route of 13534-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORYZON GENOMICS, S.A.; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; (103 pag.)WO2019/110663; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17282-40-5, 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.17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide, molecular formula is C9H12BrNO2, molecular weight is 246.1011, as common compound, the synthetic route is as follows.

General procedure: To a magnetically stirred solution of N- functionalized pyridinium, isoquinolinum, or quinolinium salt 1, 4, or 5 (1 mmol) and triphenylphosphine (1 mmol) in 3 mL DMF was added solution of alkyl propiolate 2 (1 mmol) in 2 mL DMF at -5-0 C temperature. The reaction mixture stirred for 12 h, and then the mixture was poured onto H2O (5 mL), extracted with AcOEt (15 mL), dried (MgSO4), and the solvent was removed under reduced pressure. The residue was separated by silica gel (Merck 230-240 mesh) column chromatography using hexane-ethyl acetate mixture as eluent.

Statistics shows that 17282-40-5 is playing an increasingly important role. we look forward to future research findings about 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide.

Reference:
Article; Hashemi, Seyed Abolghasem; Khalili, Gholamhossein; Synthetic Communications; vol. 45; 21; (2015); p. 2491 – 2497;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6937-03-7, Methyl 2-aminoisonicotinate, 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, 6937-03-7, blongs to pyridine-derivatives compound. SDS of cas: 6937-03-7

Compound 2E: methyl 2-((tert-butoxycarbonyl)amino)isonicotinate Methyl 2-aminopyridine-4-carboxylate (2 g, 13.14 mmol, 1.00 equiv) was dissolved in tert-butanol (20 mL) after which di-tert-butyl dicarbonate (4.02 g, 18.42 mmol, 1.40 equiv) was added. The reaction mixture was agitated at 60 C. overnight then the reaction was halted through the addition of an aqueous 1M NaHCO3 solution (50 mL). The solid was recovered by filtration, washed with 50 mL of EtOH then dried in vacuo to yield 2.5 g (75%) of compound 2E in the form of a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6937-03-7, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Goetsch, Liliane; Jouhanneaud, Alexandra; Perez, Michel; (95 pag.)US2017/112943; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 20265-38-7, 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. 20265-38-7, name is 2-Methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

A) Preparation of 3-(tert-Butoxycarbonylamino)-2-methoxypyridine STR12 To a stirred solution of 2.48 g (20 mmol) of 3-amino-2-methoxypyridine and 4.37 g (20 mmol) of di-tert-butyldicarbonate (Boc2 O) in 10 mL of THF was added at 0 C. 40 mL of a 1M solution of NaHMDS in THF. The mixture was then stirred at room temperature for 2 hours. The THF was removed by rotary evaporation and the residue was dissolved in EtOAc and washed twice with an equal volume of 0.1N HCl. The EtOAc layer was dried (MgSO4) and concentrated to give 3.9 g (87%) of the desired material as an oil after purification further by flash chromatography on silica gel using 95:5 hexane:EtOAc as the eluant.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20265-38-7, 2-Methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5532358; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1452-63-7 ,Some common heterocyclic compound, 1452-63-7, molecular formula is C6H7N3O, 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.

General procedure: To a solution of acid hydrazide in anhydrous 5-15mL of DMF, carbon disulfide (2.5mL/mmol) was added at room temperature and under a nitrogen atmosphere. The reaction mixture was then heated to 40C for 15min and then to 70C for 4-8h until the reaction was completed. After completion, the reaction mixture was cooled to room temperature and poured dropwise into ice cold water. The solids formed were separated by filtration, washed with water and dried in vacuo.

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. 1452-63-7, Picolinohydrazide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kummari, Lalith K.; Butler, Mark S.; Furlong, Emily; Blundell, Ross; Nouwens, Amanda; Silva, Alberto B.; Kappler, Ulrike; Fraser, James A.; Kobe, Bostjan; Cooper, Matthew A.; Robertson, Avril A.B.; Bioorganic and Medicinal Chemistry; vol. 26; 20; (2018); p. 5408 – 5419;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 62774-90-7, 2,6-Dichloro-4-methylnicotinic 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, Product Details of 62774-90-7, blongs to pyridine-derivatives compound. Product Details of 62774-90-7

2,6-Dichloro-4-methyl-nicotinic acid (0.234 g, 1.14 mmol) and hydrogen peroxide- urea adduct (0.537 g, 5.70 mmol) were suspended in CH2Cl2 to give a white slurry. Trifluoroacetic anhydride (0.65 ml, 4.67 mmol) was added dropwise over 5 minutes and the resulting pale yellow solution was stirred overnight at rt. The reaction mixture was quenched with water (10 ml) and then dry loaded onto silica gel and purified using column chromatography (MeCN/MeOH/NH4OH, 8:1:1, v/v/v) to give 2,6-dichloro-4-methyl-nicotinic acid-iV-oxide as a pale yellow crystalline solid (0.103 g, 41 %). 1H NMR (CD3OD ) delta 2.37 (s, 3H), 7.60 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62774-90-7, 2,6-Dichloro-4-methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ANORMED INC.; WO2006/138350; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62068-78-4, 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 62068-78-4 as follows.

6-Chloro-2-[(2-methoxy-ethyl)-methyl-amino]-nicotinamide (3) (1007) To a solution of 2,6-dichloro-nicotinamide (1) (10 g, 52.9 mmol) in acetonitrile (anhydrous, 200 mL) was added (2-methoxy-ethyl)-methyl-amine (2) (18.8 g, 212 mmol). The reaction was heated at 60 C. for 1.5 hours. 5% NaOH solution (1000 mL) was slowly added. The solution was then extracted with EtOAc (3¡Á250 mL). The combined organic layer was dried over MgSO4, filtered, and evaporated in vacuo. Purification was accomplished by silica gel chromatography, eluting with 5%-30% EtOAc/hexanes gradient, to afford 11.66 g (91% yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.07 (d, J=8.6 Hz, 1 H), 7.76 (br. s., 1H), 6.93 (d, J=8.2 Hz, 1H), 5.66 (br. s., 1H), 3.66-3.51 (m, 4H), 3.32 (s, 3H), 2.93 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62068-78-4, its application will become more common.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; US2015/291629; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem