Tag: M.W:200-300

Electric Literature of 13959-02-9 ,Some common heterocyclic compound, 13959-02-9, molecular formula is C6H4BrNO2, 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: (a) Halopicolinic acid (2.69 g, 13.31 mmol), phenylboronic acid(2.44 g, 19.97 mmol), 2M aqueous potassium carbonate (20 mL), palladiumacetate (0.14 g, 0.62 mmol), triphenylphosphine (0.70 g,2.67 mmol), and 1,4-dioxane (50 mL) were mixed and refluxed undernitrogen for 24 h. The reaction mixture was cooled to room temperatureand added aqueous sodium hydroxide (NaOH) (1 M, 35 mL) and dichloromethane(CH2Cl2) (20 mL). The aqueous layer was acidified topH=2-3 by using citric acid (1 M) followed by extraction with Etheracetate (EtOAc). The combined organic layers were dried over magnesiumsulfate (MgSO4), filtered, and concentrated to give off the crudeproduct. A mixture of the crude product and 50 g polyphosphoric acidwas heated at 210 C for 5 h and then stop the reaction. After themixture had cooled to 140 C, some ice and water were added slowly todilute the mixture. Then aqueous sodium hydroxide was added to makethe pH?7, and the aqueous layer was extracted with EtOAc. Thecombined extracts were dried with MgSO4 and concentrated to provide0.96 g. The residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate 6:1) to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13959-02-9, its application will become more common.

Reference:
Article; Wu, Peng; Zhu, Jun; Zhang, Zhen; Dou, Dehai; Wang, Hedan; Wei, Bin; Wang, Zixing; Dyes and Pigments; vol. 156; (2018); p. 185 – 191;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 52605-98-8, name is 5-Bromo-2,3-dimethoxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrNO2

Step 2. N-(6-(5,6-dimethoxypyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide Following the procedure described for N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 19), N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (0.132 g, 0.627 mmol) was reacted with bis(pinacolato)diboron (0.207 g, 0.815 mmol), DMSO (6.00 mL, 84.5 mmol) and potassium acetate (0.246 g, 2.51 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.050 g, 0.062 mmol, Strem Chemical, Inc., Newburyport, Mass.) for 6 h.

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, 52605-98-8, 5-Bromo-2,3-dimethoxypyridine.

Reference:
Patent; Booker, Shon; Kim, Tae-Seong; Liao, Hongyu; Liu, Longbin; Norman, Mark H.; Peterson, Emily Anne; Stec, Markian; Tamayo, Nuria A.; US2009/163489; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80194-68-9, 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, molecular formula is C7H3ClF3NO2, 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.

Production Example 17(1) A mixture of N2-methyl-5-pentafluoroethyl-pyridin-2 , 3- diamine (590 mg) , 3-chloro-5-trifluoromethyl-pyridin-2- carboxylic acid (560 mg) , WSC (520 mg) , HOBt (35 mg) , and pyridine (5 ml) was stirred at room temperature for 5 hours To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give intermediate compound (M20-17) .

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 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKAHASHI, Masaki; TANABE, Takamasa; ITO, Mai; NOKURA, Yoshihiko; IWATA, Atsushi; WO2013/18928; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 100366-75-4, 2-Iodo-5-trifluoromethylpyridine, 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, Recommanded Product: 2-Iodo-5-trifluoromethylpyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Iodo-5-trifluoromethylpyridine

General procedure: In a glove box, a flame-dried pressure Schlenk tube was charged with NaI(0.3 equiv). The Schlenk tube was taken out of the glove box and charged with amide 1 (1.5equiv), iodopyridine reagent (1 equiv), Ag2CO3 (1.5 equiv), (BnO)2PO2H (0.2 equiv) andPd(OAc)2 (0.1 equiv). DMA and Toluene (1:20 in v/v ratio, 0.1 M) were added. The tube wastightly closed and flushed with argon by three freeze-pump-thaw cycles. The mixture was stirredat 130 C for 24 h. Subsequently, it was diluted with EtOAc (40 mL) and washed with brine (2 ×20 mL) and water (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated invacuo. The crude product was purified by flash chromatography (hexane/ EtOAc in 85/15 to 50/50v/v ratio). Unless otherwise noted, the reactions were run on 0.1 mmol scale.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100366-75-4, 2-Iodo-5-trifluoromethylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Hu, Peng; Bach, Thorsten; Synlett; vol. 26; 20; (2015); p. 2853 – 2857;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-84-1, 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. 128071-84-1, name is 4-Bromo-2-chloropyridine-3-carboxaldehyde. A new synthetic method of this compound is introduced below.

Example 104b 2-Chloro-4-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehyde 104b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 104a (1.1 g, 5.0 mmol), 3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 101e (477 mg, 2.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (230 mg, 0.25 mmol), XantPhos (430 mg, 0.75 mmol), Cs2CO3 (1.6 g, 5.0 mmol), and 1,4-dioxane (50 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65C for 2 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (40:1) to afford 104b as a yellow solid (1.1 g, 80%). MS: [M+H]+ 330.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-84-1, its application will become more common.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59237-53-5 , The common heterocyclic compound, 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, 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.

[0202] A solution of methyl 6~chloro-5-nitronicotinate (5 g, 23.09 mmol), 4~(2,,4~ difluorophenoxy)piperidine hydrochloride (6.92 g, 27.7 mmol) and K2CO3 (9.57 g, 69.3 mmol) in ACN (57.7 mL) was stirred at 80°C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 250 mL). The organic layers were combined, dried over NazSC and filtered. The filtrate was concentrated in vacuo and purified by column chromatography (ISCO column) elutmg with a gradient of 0-100percent EtOAc in heptane, to give the title compound as a yellow solid (6.04 g, 66.5percent). lR NMR (500 MHz, DMSO-afe) delta ppm 1.74 (dq,./ 12. KK. 4.17 Hz, 2 I .}. 2.04 (ddd, J=9.76, 6.83, 3,42 Hz, 2 H), 3.45 (td, 7=8.91, 4.15 Hz, 2 H), 3.71 – 3.76 (m, 2 H), 3.85 (s, 3 H), 4,66 (tt, J=7.51, 3,72 Hz, 1H), 7.00 – 7,06 (m, 1H), 7.27 – 7.36 (m, 2 H), 8.56 (d,/ 1.46 Hz, 1H), 8.82 (d,,/ 1.46 Hz, 1H); ESI-MS m/z | M I I . 394.2.

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 186593-42-0, 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. 186593-42-0, name is 3-Bromo-2-methyl-5-nitropyridine. A new synthetic method of this compound is introduced below.

4-(2-Methyl-5-nitropyridin-3-yl)-N-neopentyIbenzenesulfonamide. The compound obtained above (30 mg, 0.085 mmol), 3-bromo-5-nitro-2-methylpyridine (1.0 eq., 18 mg), K2CO3 (3 eq., 35 mg) and Pd(PPh3)4 (10 mol %, 10 mg) were dissolved in 3 ml DMErEtOH (9: 1). The solution was stirred at 800C for 24 hr under nitrogen. The mixture was concentrated in vacuo. Column chromatography (SiOa; 3:1 Hex: EtOAc) yielded 20 mg of the target compound. (CaIc. mass: 364, obs. mass 364).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,186593-42-0, 3-Bromo-2-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; KEMIA, INC.; WO2008/21388; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886373-00-8, Adding some certain compound to certain chemical reactions, such as: 886373-00-8, name is 5-Bromo-2-ethoxypyridin-3-amine,molecular formula is C7H9BrN2O, 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 886373-00-8.

Intermediate 61 lambda/-[5-Bromo-2-(ethyloxy)-3-pyridinyl]benzenesulfonamide A solution of 5-bromo-2-(ethyloxy)-3-pyridinamine (1.45 g) in anhydrous pyridine (15 ml) was treated with benzenesulfonyl chloride (1.03 ml) then stirred at RT for 20 hr. The reaction was evaporated to dryness and the residue was purified by column chromatography on silica, eluting with 30% hexanes in DCM, to give the title compound (1.86 g).1H NMR: deltaH (DMSOd6, 400 MHz) 10.09 (1 H, s), 8.03 (1 H, d), 7.74 (1 H, d), 7.71 (1 H, d), 7.64 (1 H, d), 7.57 (2H, d), 4.05 (2H, q), 1.07 (3H, t).

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. 886373-00-8, 5-Bromo-2-ethoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147187; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 145325-40-2 ,Some common heterocyclic compound, 145325-40-2, molecular formula is C9H6BrNO2S, 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.

4-Methylene-piperidine-1-carboxylic acid benzyl ester (250 mg, 1.08 mmol) is dissolved in a 0.5 M solution of 9-Bora-bicyclo[3.3.1]nonane in THF (2.16 ml, 1.08 mmol) and heated at 67C for 1.5 hour. The mixture was cooled and Pd C12 dppf (40.8 mg, 0.05 mmol), Cs2CO3 (0.98 g, 3.00 mmol) and a solution 4-Bromo-thieno[2,3-c]pyridine-2- carboxylic acid methyl ester (272 mg, 1.00 mmol) in p=Dioxane (3.0 ml) were added. The mixture was de-gassed and heated at 90C for 3 hours. The mixture was cooled and filtered through silica gel, chasing with EtOAc. The organic layer was concentrated and the residue was further purified by flash chromatography on silica gel using 4 : 1/ CH2CL2 : EtOAc , then 1 : 1/ CH2CL2 : EtOAc as eluant. Product fractions were combined and concentrated to yield 128 mg (30%) of 4-(1-Benzyloxycarbonyl piperidin-4-ylmethyl)-thieno@2,3-cJpyridine- 2-carboxylic acid methyl ester as a yellow solid; RP-HPLC (Table 1, Method M), Rt 2.40 min; m/z: (M + H) + 425.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145325-40-2, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/110410; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52605-98-8, 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.52605-98-8, name is 5-Bromo-2,3-dimethoxypyridine, molecular formula is C7H8BrNO2, molecular weight is 218.05, as common compound, the synthetic route is as follows.

5,6-Dimethoxynicotinaldehyde (42) To a solution of 5-bromo-2,3-dimethoxypyridine (41, 21.7 g, 99.5 mmol) in anhydrous tetrahydrofuran (200 mL) was dropwise added n-butyl lithium (48.0 mL, 2.5 mol/L in hexane) at -78 C. under N2. The mixture was stirred for at -78 C. for 1 h. Then N, N-dimethylformamide (16.2 mL) was added to the mixture at -78 C. The reaction mixture was stirred for another 30 min at -78 C. After the reaction was completed, the mixture was quenched by saturated NH4Cl(sat.), extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo. The residue was purified by flash chromatogram with ethyl acetate/petroleum ether (1:3) to afford 5,6-dimethoxynicotinaldehyde (42) as a yellow solid (13.5 g, 81%). ESI-MS, m/z=168 [M+H]+.

Statistics shows that 52605-98-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,3-dimethoxypyridine.

Reference:
Patent; Tsai, Guochuan Emil; Wang, Ching-Cheng; Hsieh, Yuan-Ting; (53 pag.)US2019/112289; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem