Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 97966-00-2, 5-Bromo-2,3-dichloropyridine, 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: C5H2BrCl2N, blongs to pyridine-derivatives compound. COA of Formula: C5H2BrCl2N

To a solution of 5-bromo-2,3-dichloropyridine (29) (702 mg, 3.09 mmol) in THF (7 ml) was dropwise added isopropylmagnesium chloride lithium chloride complex (3.09 ml, 4.02 mmol) at 0 C. for 10 min. Then N-methoxy-N-methylacetamide (658 mul, 6.19 mmol) in THF (2 ml) was dropwise added to the reaction mixture at the same temperature and stirred at for 2 hrs. Then the reaction mixture was quenched with aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting product was chromatographed on silica gel eluting with a gradient of hexane/ethyl acetate (5-15%) to afford 232 mg of the desired product (30) in 40% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.91 (1H, s), 8.55 (1H, s), 2.65 (3H, s).

The synthetic route of 97966-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89364-04-5, 3-Bromo-4-nitropyridine, 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 C5H3BrN2O2, blongs to pyridine-derivatives compound. Computed Properties of C5H3BrN2O2

Step 5: 5-(2,3-difluoro-4-(4-nitropyridin-3-yl)phenyl)-2-((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl)oxy)pyridine To a solution of 5-(2,3-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-2-((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl) oxy) pyridine (350 mg, 0.544 mmol) in dioxane/H2O (11 mL, 10/1, v/v) was added 3-bromo-4-nitropyridine (121 mg, 0.6 mmol), Na2CO3 (120 mg, 1.1 mmol) and Pd(PPh3)4 (63 mg). The mixture was stirred at 110 C. for 1h under N2. After the reaction, the mixture was extracted with ethyl acetate (20 mL) and washed with brine (30 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated. The crude was purified by column chromatography on silica gel with PE/EA (1:3) to give the desired product (170 mg) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89364-04-5, 3-Bromo-4-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-12-8, Adding some certain compound to certain chemical reactions, such as: 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate,molecular formula is C17H19NO2, 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 1083057-12-8.

Preparation of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0.3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2SO3 (1.5 eq) was added via addition funnel. After completion of Na2SO3 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2CO3 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that was used directly in the next step.

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Verwijs, Marinus Jacobus; (75 pag.)US2016/324788; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1044872-40-3, 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. 1044872-40-3, name is Methyl 2-amino-4,6-dichloronicotinate, molecular formula is C7H6Cl2N2O2, 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.

Example 13. Preparation of 2-(4-(2-(benzyloxy)ethoxy)-3,5-dimethylphenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-one [0196] A mixture of dimethyl acetone-1,3-dicarboxylate (200 g 1.148 mol), cyanamide (48.3 g, 1.148 mol), and Ni(acac)2 (14.75 g, 0.0574 mol) in dioxane (200 mL) was heated to reflux in a 1-L flask with a reflux condenser. The reaction mixture was heated at reflux for 16 hours and then cooled to room temperature. The precipitate was filtered off, and the solid was mixed with methanol (200 mL), stirred for 30 minutes, and filtered again to give methyl 2-amino-4-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate (93 g, 44%). [0197] In a 1-L flask with a reflux condenser was added methyl 2-amino-4- hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate (93.0 g, 0.505 mol) and POCI3 (425 ml_) and the reaction mixture was heated to reflux for 35 minutes. About 300 ml_ POCI3 was evaporated under vacuum. The residue was poured into ice and water (400 ml_), which was further neutralized with KOH to pH approximately 6-7. The precipitate was filtered off and extracted with ethyl acetate (2 x 300 ml_). The organic solution was concentrated and passed through a column, eluting with hexane:ethyl acetate 4:1 , to give methyl 2-amino-4,6-dichloropyridine-3-carboxylate (22.5 g, 20.1%).[0198] In a 500-mL flask with a reflux condenser was added methyl 2- amino-4.6-dichloropyridine-3-carboxylate (22.5 g, 0.101 mol) and 25 wt% sodium methoxide in methanol (88 mL, 0.407 mol), together with methanol (20 ml_). The mixture was heated to reflux for 5 hours, then cooled to room temperature. Acetic acid (15 mL) was added to the mixture and pH was adjusted to approximatley 7. Methanol was removed and the residue was poured into water (100 mL). The precipitated solid was filtered and further rinsed with water (3 * 200 mL) to give methyl 2-amino-4, 6-dimethoxypyridine-3-carboxylate (18.5 g, 86.4%).[0199] In a 500-mL flask with a reflux condenser was added methyl 2-amino-4,6-dimethoxypyridine-3-carboxylate (18.5 g, 0.0872 mol), potassium hydroxide (19.5 g, 0.349 mol) in water (80 mL) and ethanol (100 mL). The mixture was heated to 800C for 16 hours. The solvent was removed and aqueous HCI was used to adjust the pH to 6. The water was removed by freeze drying. The obtained solid was extracted with methanol to yield 2-amino-4,6-dimethoxy-nicotinic acid (17.2 g, 100%).[0200] 2-Amino-4,6-dimethoxy-nicotinic acid (17.2 g, 0.0872 mol) was added to THF (110 mL). 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (21.73 g, 0.113 mol), 1-hydroxybenzotriazole hydrate (12.96 g, 0.0959 mol) and 4-methyl morpholine (9.7 g, 0.0959 mol) were then added to the suspension. After stirring for 10 minutes at room temperature, 50% v/v ammonium hydroxide (18.3 g, 0.262 mol) was added. The reaction mixture was kept at room temperature for 16 hours. THF was removed and the residue was poured into cold water (100 mL). The precipitate was filtered off and washed with cold water to yield 2-amino-4,6-dimethoxy-nicotinamide (10.8 g, 62.3%). [0201] To a solution of 4-hydroxy-3,5-dimethylbenzaldehyde (6.84 g, 0.0455 mol) in anhydrous DMF (15 ml_) was added NaH in mineral oil (60%, 2.23 g, 0.0558 mol). (2-Bromo-ethyoxymethyl)-benzene (10.0 g, 0.0465 mol) was added and the reaction was kept at 65C overnight. The reaction mixture was poured into water and extracted with dichloromethane to yield (4-(2-benzyloxy-ethoxy)-3,5-dimethylbenzaldehyde (10.5 g, 81%), which was used for next step reaction without further purification.[0202] To a solution of 2-amino-4,6-dimethoxy-nicotinamide (2.55 g, 12.9 mmol) and 4-(2-benzyloxy-ethoxy)-3,5-dimethylbenzaldehyde (3.68 g, 12.9 mmol) in N,N-dimethyl acetamide (20 ml_), were added NaHSO3 (2.52 g, 14.2 mmol) and p-TSA (1.98 g, 10.4 mmol). The reaction mixture was heated at 1500C for 14 hours. The reaction mixture was cooled to room temperature. The solvent was removed under reduced pressure. The residue was diluted with water and the solid was collected and further washed with methanol. The crude product was purified by column chromatography (silica gel 230-400 mesh; 2% methanol in CH2CI2 as eluent) to give the title compound as an off-white solid (0.88 g, 14.7%). MP 204.5-205.90C.

According to the analysis of related databases, 1044872-40-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RESVERLOGIX CORP.; HANSEN, Henrik, C.; WAGNER, Gregory, S.; ATTWELL, Sarah, C.; MCLURE, Kevin, G.; KULIKOWSKI, Ewelina, B.; WO2010/123975; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 117846-58-9, 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.117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, molecular weight is 264.95, as common compound, the synthetic route is as follows.

To a stirred anhydrous THF solution of 4 (3.22 g,12.15 mmol) was added dropwise a 2.4 mol L-1 n-BuLi inhexane solution (5.57 mL, 13.37 mmol) at 195 K under argonatmosphere. Stirring continued for 0.5 h at 195 K; a solutionof (2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene(4.90 g, 13.37 mmol) in THF was added and the reactionmixture was stirred for 1 h at this temperature. The reactionwas quenched by addition of water. After being extractedwith dichloromethane, the organic layer was washed withwater, and dried over anhydrous Na2SO4. The crude productwas purified by column chromatography on Al2O3 usingpetroleum ether as eluent to afford 6 (1.96 g, 28%) as a whitesolid. m.p. 86-87 C; 1H NMR (400 MHz, CDCl3) d 1.83(s, 3H, -CH3), 2.00 (s, 3H, -CH3), 2.29 (s, 3H, -CH3), 7.10(s, 1H, thiophene-H), 7.25 (t, 2H, J 8.0 Hz, benzene-H), 7.33 (t, 2H, J 8.0 Hz, benzene-H, pyridine-H), 7.48 (d, 2H,J 4.0 Hz, benzene-H).

The chemical industry reduces the impact on the environment during synthesis 117846-58-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Liao, Guanming; Xue, Dandan; Zheng, Chunhong; Wang, Renjie; Pu, Shouzhi; Journal of the Brazilian Chemical Society; vol. 27; 11; (2016); p. 1989 – 1997;,
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. 1000339-23-0, name is 2-Amino-5-bromoisonicotinic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C6H5BrN2O2

A mixture of compound 14-2 (7.81 g, 35.6 mmol), DPPA (9.40 mL, 43.5 mmol) and Et3N (5.90 mL, 42.5 mmol) in i-BuOH (300 mL) was stirred at 90 C for 6 hrs under an atmosphere of N2. The solvent was removed and the residue was purified by silica gel column chromatography (Petroleum ether/EtOAc = 5/1 to 4/1 (v/v)) to give compound 14-3 (4.9 g, 47% yield) as a white solid. LC-MS (ESI): m/z 234 [M-56+H]+.

The synthetic route of 1000339-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDIO PHARMACEUTICALS, INC.; ZHONG, Min; LI, Leping; WO2012/58125; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5BrClN

Step 3; Preparation of 3-oxopiperazine-1-carboxyimidothionic acid 6-bromopyridin-2-ylmethyl ester 2-Bromo-6-chloromethylpyridine (1.50 g, 7.26 mmol) obtained in Step 1 was dissolved in ethanol (15 ml) and 3-oxopiperazine-1-carbothionic acid amide (1.16 g, 7.29 mmol) obtained in Step 2 was added, and the mixture was heated to reflux for 2 hours. After the reaction solution was cooled to room temperature, the solution obtained by vacuum concentration was neutralized with a saturated aqueous sodium bicarbonate, and the precipitated solid was separated by filtration, washed with water and the title compound (1.67 g, 70%) was obtained.

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, 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117846-58-9, 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.117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, molecular weight is 264.95, as common compound, the synthetic route is as follows.

To a solution of 2,6-dibromo-3,5-dimethylpyridine (1.0 g, 3.77 mmol) in toluene (30 mL) was added n-BuLi (1.5 mL, 3.77 mmol) dropwise at -78 C. After 1 h, DMF (358 mg, 4.9 mmol) was added to the mixture for additional lh. The mixture was adjusted to pH = 34 using HC1 and extracted with EtOAc (50 mL x 3) and the organic layers were concentrated and purified by chromatography (silica, ethyl acetate/petroleum ether =1/10) to afford 6-bromo-3,5- dimethylpicolinaldehyde (242 mg, 1.13 mmol, 30%) as a white solid. ESI-MS (EI, m/z): 214.1 [M+H].

Statistics shows that 117846-58-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-3,5-dimethylpyridine.

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: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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 89415-54-3, blongs to pyridine-derivatives compound. Product Details of 89415-54-3

In a flask were combined 2-methylpropanamide (Aldrich, cat144436: 285 mg, 3.28 mmol), THF (2 mL) and triethyloxonium tetrafluoroborate (Aldrich, cat90520: 0.617 g, 3.25 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in ethanol (1.9 mL). To this residue was added a suspension of 5-bromo-N2-methylpyridine-2,3-diamine (200 mg, 0.99 mmol) [Combi-Blocks cat AN-3965] in ethanol (6.7 mL). The mixture was then stirred at 80 C. for 1 hour. After the crude reaction mixture had cooled to room temperature the solvent was removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 20% MeOH/DCM to give the desired product (48 mg, 19% yield). LC-MS calculated for C10H13BrN3 (M+H)+: m/z=254.0. found 254.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 7477-10-3

Synthesis (compoundof 6- (4-Ethoxyphenylamino) -5-nitronicotinic acid 22-2)[0000150] To a solution of 6-chloro-5-nitronicotinic acid (22-1) (10 g, 49 mmol, 1.0 equiv) in acetonitrile (150 mL) was added triethylamine (15.1 mL, 109 mmol, 2.2 equiv) and 4- ethoxyaniline (6.7 mL, 52 mmol, 1.05 equiv) . The mixture was heated refluxed for 18 hours and concentrated under reduced pressure. The residue was suspended in water (100 mL) and the pH adjusted to 4 with 6N hydrochloric acid. The aqueous phase was extracted with a 2:1 mixture of ethyl acetate and tetrahydrofuran (4 x 100 mL) . The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to give crude compound 22-2 (14 g, 96% yield) as a black 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, 7477-10-3, 6-Chloro-5-nitronicotinic acid.

Reference:
Patent; SIGA TECHNOLOGIES, INC.; DAI, Dongcheng; BURGESON, James, R.; AMBERG, Sean, M.; HRUBY, Dennis, E.; WO2013/123215; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem