Tag: M.W:200-300

Application of 28733-43-9, Adding some certain compound to certain chemical reactions, such as: 28733-43-9, name is 5-Bromonicotinamide,molecular formula is C6H5BrN2O, 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 28733-43-9.

To a solution of NaOH (22.9 g, 572 mmol) in water (245 mL) at 0-5 C. (ice salt bath) was added bromine (9.44 mL, 184 mmol) maintaining the temperature at 0-5 C., to produce a sodium hypobromite solution. To this NaOBr-sol. was added commercially available 3-bromonicotinamide (30.15 g, 150 mmol) all at once with vigorous stirring. After being stirred for 15 min, the solution is clear and mixture was heated to 70-75 C. for 45 min. Cooled to 23 C., saturated with solid NaCl, extracted with TBME/THF (3×300 mL), dried over Na2SO4. Removal of the solvent in vacuum gave a dark brown oil which was purified by silica gel column chromatography with heptane/EtOAc 1:1?2:3 to give the title compound as a brown solid (16.036 g, 62%). MS (ISP) 173.1 [(M+H)+], 175.2 [(M+2+H)+].

According to the analysis of related databases, 28733-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Palmer, Wylie Solang; Wichmann, Juergen; Woltering, Thomas Johannes; US2006/217387; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1279815-46-1, 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.1279815-46-1, name is 1-(2-Bromopyridin-4-yl)cyclopropanecarbonitrile, molecular formula is C9H7BrN2, molecular weight is 223.0693, as common compound, the synthetic route is as follows.

To a solution of l-(2-bromo-pyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.20 mmol) in toluene (30 mL) is added DIBAL-H (10.4 mL, 1M in toluene) at -78C. The mixture is stirred 1 hour at -78C and warmed to room temperature. After 1 hour, ethyl acetate (30 mL) is added, followed by 1M aqueous solution of H2S04 (30 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3 x 50 mL). The combined organic layers are dried over MgS04, filtered and concentrated to afford crude l-(2-bromo-pyridin-4-yl)-cyclopropanecarbaldehyde (ES+ m/z 226.48; 228.47), which is used without purification.

The chemical industry reduces the impact on the environment during synthesis 1279815-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; MAO, Can; RAZAVI, Hossein; WO2011/49917; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 929617-30-1 ,Some common heterocyclic compound, 929617-30-1, molecular formula is C7H6BrN3, 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.

To a 500 mL round bottom flask containing 75 mL dry THF was dissolved 5- bromo-3-methyl-1 /-/-pyrazolo[3,4-c]pyridine (5.5 g, 25.9 mmol), and the contents were cooled to -15 0C. Sodium hydride (1.24 g (60% by wt., 31.1 mmol) was slowly added in portions to the cold stirring mixture, wherein vigorous gas evolution was observed (NOTE: Use caution during handling and addition of sodium hydride). After stirring for 15 min, benzenesulfonyl chloride (3.66 ml_, 28.5 mmol) was added dropwise via syringe. After stirring 15 min, the contents were removed from the cold bath and stirred with warming to room temperature over a 3 h period. The reaction mixture was poured onto a vigorously stirred solution of ice:water (1 :1 , 500 g), upon which the solid product crashes out. After stirring an additional 10 min, the heterogenous mixture was vacuum filtered and the filter cake was washed with additional water. The resultant solid was triturated with methanol (30 ml_), and the title compound is obtained as an off-white solid (10.75 g, 82%). 1H NMR: (CD3OD- d4) 9.27 (s, 1 H), 8.05 (s, 1 H), 8.01 (d, 2H), 7.69-7.73 (m, 1 H), 7.57-7.61 (m, 2H), 2.53 (s, 3H) ; LC/MS (MH+) = 351.8, 353.8; RT = 2.05 min.

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. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32651; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, 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 solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product. 1H NMR (500 MHz, DMSO- , 5 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC MS (M+l)+ – 169.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; SHI, Zhi-Cai; CATO, Brian; KIM, Esther, Y.; WO2013/66718; (2013); A2;,
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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromo-2-chloro-5-methylpyridine

A mixture of 66 (0.35g, 1.02mmol), 4-bromo-2-chloro-5-methylpyridine (0.32g, 1.53mmol) and K3PO4 (0.43g, 2.04mmol) in dioxane (15mL) was exchanged with argon twice, then PdPPh3)4 (0.11g, 0.1mmol) were added to the above mixture. The reaction mixture was heated to 100C and stirred for 4h under argon atmosphere. The mixture was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in 74 petroleum ether 5%) to give the product as a white solid (0.3g, yield=69%). 1H NMR (400MHz, CDCl3) delta 8.25 (s, 1H), 7.64 (m, 2H), 7.19 (s, 1H), 4.07 (d, J=7.0Hz, 2H), 3.99 (dd, J=11.3, 3.2Hz, 2H), 3.35 (td, J=11.8, 2.1Hz, 2H), 2.49 (s, 3H), 2.22-2.16 (m, 1H), 1.60 (s, 9H), 1.50-1.42 (m, 3H). LC/MS (ESI, m/z) 424.14 [M+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, 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine.

Reference:
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
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. 58484-01-8, name is 3-Amino-2,6-dichloroisonicotinic acid, molecular formula is C6H4Cl2N2O2, 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. Product Details of 58484-01-8

Step 4 : Preparation of 6, 8-dichloro-2- [2- (3-chloro-pyridin -2-yl) -5-trifluoromethyl-2ff-pyrazol-3-yl] -pyrido [3, 4-d] [1, 3] oxazin-4-one; 5-Trifluoromethyl-2- (3-chloro-pyridin-2-yl) -2H-pyrazole-3- carboxylic acid chloride (example 2, step 3) (242 mg) was added to a mixture of 3-amino-2 , 6-dichloroisonicotinic acid (example 1, step 8) (190 mg) in acetonitrile (3 mL) . The mixture was stirred for 5 minutes at room temperature and triethylamine (220 muL) was added and stirred for 20 minutes, before a second portion of triethylamine (220 muL) was added. After the mixture was stirred for further 20 minutes at room temperature, methanesulfonyl chloride (70 muL) was added. After stirring for 2 hours at room temperature, the formed precipitate was filtered off, washed carefully with water and MTB-ether and dried in vacuum to afford 350 mg of the title compound of the formulaas a yellow solid. 1H-NMR (CDCl3, TMS) 6 (ppm) : 7.54-7.57 (2H, m) , 7.88 (IH, s), 8.01-8.04 (IH, m) , 8.56-8.58 (IH, m) .

With the rapid development of chemical substances, we look forward to future research findings about 58484-01-8.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, name: 2-(Bromomethyl)-6-methoxypyridine, blongs to pyridine-derivatives compound. name: 2-(Bromomethyl)-6-methoxypyridine

Substitution of 2-bromomethyl-6-methoxypyridine for 2-chloromethyl-3-methoxypyridine in the general procedure of Example 1(iii)-(v) leads to the preparation of N-cyano-N’-methyl-N”-[2-((6-methoxy-2-pyridyl)methylthio)ethyl]guanidine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4083983; (1978); A;,
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. 49669-13-8, name is 2-Acetyl-6-bromopyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Acetyl-6-bromopyridine

Preparation 31 Synthesis of 2-(6-bromo-pyridin-2-yl)-propan-2-ol Add a solution of methyl magnesium bromide (3.0 M, 9.7 mL, 29.09 mmol) in tetrahydrofuran dropwise over 20 min to a cooled solution of 1-(6-bromo-pyridin-2-yl)-ethanone (5 g, 24.25 mmol) in anhydrous tetrahydrofuran (48.5 mL) at 0 C. Upon completion of the reaction, add water (exothermic), dilute with ethyl acetate (50 mL) and separate the layers. Extract the aqueous layer once with ethyl acetate (50 mL). Dry the combined organic layers over sodium sulfate, filter and concentrate to give the title compound as a pale yellow liquid (5.69 g, 98%) that is used without further purification. 1H NMR (CDCl3) delta 1.55 (s, 6H), 4.07 (s, 1H), 6.59 (t, 1H), 7.37 (t, 2H), 7.55 (t, 1H).

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, 49669-13-8, 2-Acetyl-6-bromopyridine.

Reference:
Patent; Britton, Thomas Charles; Dehlinger, Veronique; Fivush, Adam Michael; Hollinshead, Sean Patrick; Vokits, Benjamin Paul; US2009/253750; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-10-3, 6-Chloro-5-nitronicotinic 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, Application In Synthesis of 6-Chloro-5-nitronicotinic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 6-Chloro-5-nitronicotinic acid

General procedure: SI, Figure 1. General procedure for the synthesis of the ester compounds (2, Scheme 1). To the commercially available acids (1a-c) (1 equiv.) in dry DCM (20 mL) was added DMAP (1 equiv.),DCC (1.2 equiv.) and various alcohols (1.2 equiv.) at 0 oC. The mixture was stirred at 0 oC for 1h then at room temperature for 17 h. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel using a mixture of solvent of hexane: ethylacetate (10:1) to provide the desired ester derivatives(2).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iniguez, Eva A.; Perez, Andrea; Maldonado, Rosa A.; Skouta, Rachid; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5315 – 5320;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1201187-18-9, 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. 1201187-18-9, name is 6-Chloro-4-(trifluoromethyl)nicotinonitrile. A new synthetic method of this compound is introduced below.

4-hydroxy was prepared in Reference Example 60 3- (piperidin-4-yl) -4- (trifluoromethyl) -1,4,5,7- tetrahydro -6H- pyrazolo [3,4-b] pyridin-6-one hydrochloride (150mg, 0.440mmol) in dimethyl sulfoxide (0.5 mL) solution of, N, N- diisopropylethylamine (89.8muL, 0.528mmol), and 6-fluoro-3- ( the compounds described in trifluoromethyl) pyridine-2-carbonitrile (US2008 / 275057 pamphlet, 136mg, 0.660mmol) was added, using a Biotage Inc. the Initiator (TM), 60 C., 20 min micro and the mixture was stirred while irradiating the waves.The reaction mixture was poured into water, and extracted twice with ethyl acetate, the resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatography was purified in the elution solvent hexane / ethyl acetate = 88 / 12-0 / 10 gradient)], the title compound (43.1mg, yield: 21%) a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1201187-18-9, 6-Chloro-4-(trifluoromethyl)nicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem