Tag: M.W:200-300

Synthetic Route of 67625-38-1, 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. 67625-38-1, name is Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

EXAMPLE 3 6-Chloro-N-(pyrazin-2-yl)imidazo[1,2-a]pyridine-2-carboxamide (No. 3 of the Table)400 mul of a 2M solution of trimethylaluminium in toluene are added dropwise to a solution, cooled to 0 C., of 120 mg of ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate and 61 mg of pyrazin-2-ylamine in 1.2 ml of toluene. The reaction mixture is heated at 70 C. for 16 hours. After evaporating the toluene, the residue is taken up in 0.1N hydrochloric acid and extracted with ethyl acetate. The combined organic phases are washed with aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue is triturated with ethyl ether to give 115 mg of 6-chloro-N-(pyrazin-2-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67625-38-1, Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2010/317673; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77837-09-3, 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.77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate, molecular formula is C13H11NO3, molecular weight is 229.23, as common compound, the synthetic route is as follows.

Step 3; 6-Oxo-l -phenyl- 1 ,6-dihydropyridine-3-carboxylic acid:; Lithium hydroxide monohydrate (0.366 g, 8.73 mmol) was added to a mixture of methyl-6-oxo-l -phenyl- 1,6- dihydropyridine-3-carboxylate (1.0 g, 4.37 mmol), tetrahydrofuran (9 mL) and water (6 mL) at 0 C. The mixture was stirred for 1 hour, diluted with water and washed with ethyl acetate. The pH of the aqueous layer was adjusted to 2 using 2 N hydrochloric acid and the precipitate was filtered to give the title compound as a brown solid (0.740 g, 79%). m.p. 256-263 C; *H NMR (400 MHz, DMSO-d6) delta 6.53 (d, / = 9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, / = 2.5, 9.8 Hz , 1H), 8.23 (d, / = 2.5 Hz, 1H); IR (KBr) upsilon 3446, 1708, 1645, 1577, 1263, 1228 cm”1; MS 214 (M – 1).

The chemical industry reduces the impact on the environment during synthesis 77837-09-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; SOMMERS, Andreas; WO2012/122165; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84199-61-1, 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.84199-61-1, name is 3-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.

4.2. Synthesis of compounds with formula 6: Reaction 1, 2, 4 and 5 of Scheme 1 The first step was made according to the following literature: M. Tiano, P. Belmont J. Organic Chem. 2008, 73, 4101-4109. The second step was carried out according to N. Nishiwaki, S. Minakata, M. Komatsu, Y. Ohshiro, Synlett 1990, 5, 273-275. Synthesis of 7-phenylquinolin-5-ol (6.1) for Example 12.7 6.1Step 1 (= reaction 1): 66 mg 3-Acetyl-2-bromopyridine, 56 mu?, phenylacetylene, 170 mu?, DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g Si02, cyclohexane cyclohexane /ethylacetate 70:30) to yield 40 mg l-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS : Rt = 1.21 min (method E), M+H = 222.

Statistics shows that 84199-61-1 is playing an increasingly important role. we look forward to future research findings about 3-Acetyl-2-bromopyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John; WO2013/14060; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 186413-75-2, Adding some certain compound to certain chemical reactions, such as: 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine,molecular formula is C6H4BrClN2O2, 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 186413-75-2.

Intermediate 4: S-Bromo-l-chloro–methyl-pyridin-S-ylamine In a 250ml RB flask, 3-bromo-6-chloro-2-methyl-5-nitropyridine (1.5 g, 5.97 mmol, commerical) was dissolved in ethyl acetate (20 mL). To this solution, ammonium chloride (3.19 g, 59.65 mmol) dissolved in water (10ml) was added and stirred at RT for 10 minutes. Then zinc powder (2.340 g, 35.79 mmol) was added at once and the resulting reaction mixture was refluxed at 550C for 6hrs. The reaction mixture was filtered through ceilite and concentrated in vacuo. The residue was partitioned between ethyl acetate (150ml) and water (75). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by Flash column chromatography using Argonaut purification system, which was eluted with 12% ethyl acetate in hexane to give 5-bromo-2-chloro-6-methylpyridin-3-amine (0.500 g, 37.8 %) as white solid. MS (ES+): 222 for C6H6BrClN2

According to the analysis of related databases, 186413-75-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84539-34-4, 4-Amino-3,5-dibromopyridine, 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, 84539-34-4, blongs to pyridine-derivatives compound. Safety of 4-Amino-3,5-dibromopyridine

3,5-Diisopropylpyridin-4-amine To a mixture of 3,5-dibromo-4-amino-pyridine (5.0 g, 19.9 mmol, AstaTech, Inc.), Cphos (0.868 g, 1.989 mmol), palladium acetate (0.223 g, 0.994 mmol), and THF (40 mL) was added 2-propylzinc bromide (1 M in THF) (80 mL, 80 mmol, Rieke Metals, Inc.) dropwise and the mixture was stirred at rt for 2 h. The reaction mixture was quenched with 5 N NaOH (100 mL), extracted with EtOAc (2*50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (eluent 0-30% DCM-MeOH (4:1)/DCM) to provide 3,5-diisopropylpyridin-4-amine (Intermediate 162, 1.4 g, 7.8 mmol, 39.4% yield) as orange syrup. 1H NMR (400 MHz, DMSO-d6) delta 7.88 (s, 2H), 5.47-5.60 (m, 2H), 3.00 (spt, J=6.8 Hz, 2H), 1.17 (d, J=6.8 Hz, 12H). m/z (ESI, +ve ion): 179.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84539-34-4, its application will become more common.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184368-74-9 ,Some common heterocyclic compound, 184368-74-9, molecular formula is C12H19NO4, 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 solution of 1 -(tert-butyl)4-methyl-3 ,6-dihydropyridine- 1 ,4(2H)-dicarboxy-late (1.7 g, 7.3 mmol) in DCM (20 ml) at -78 C was added DIBAL-H (1.0 M in toluene,10.5 ml, 10.5 mmol) followed by stirring at RT for 16 h. The reaction was cooled to 0C and quenched with water and extracted with DCM. The organic layer was dried,filtered and concentrated under reduced pressure to give 1.5 g of the title compound asgreenish viscous liquid. LC-MS: mlz 214 (M+H) +.

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. 184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORION CORPORATION; DIN BELLE, David; MAeKELAe, Mikko; PASSINIEMI, Mikko; PIETIKAeINEN, Pekka; RUMMAKKO, Petteri; TIAINEN, Eija; VAISMAA, Matti; WOHLFAHRT, Gerd; (254 pag.)WO2018/115591; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84199-61-1 ,Some common heterocyclic compound, 84199-61-1, molecular formula is C7H6BrNO, 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.

Step 1 (= reaction 1): 100 mg 3-Acetyl-2-bromopyridine, 140 mg 5-ethynyl- 1 ,2,3- trimethoxybenzene 2Lambda, 101 triethylamine, 17 mg triphenylphosphinpalladium(II) chlorid, 1 mg Cu(I)I were suspended in 4 mL THF under argon atmosphere and stirred for 1 h at 25C. The mixture was diluted with DCM and extracted with diluted aq. N¾ and saturated NH4CI solution. The orgranic phase was concentrated and the the mixture separated via FCC (10 g S1O2, Cyclohexane -> cyclohexane /ethylacetate 70:30) to yield 90 mg l-(2-(3,4,5- trimethoxyphenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt = 1.21 min (method E) M+H = 312.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84199-61-1, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John; WO2013/14060; (2013); 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.867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrClN

General procedure: General Procedure A: (0312) A mixture of an arylbromide or aryliodide (1 mmol), an arylboronic acid, aryldioxaborolane or bis(pinacolato)diboron (1.5 mmol), a palladium catalyst (0.1 mmol) and K2CO3 (2-3 mmol) was placed in a reaction vessel which was then thoroughly purged with argon. Dioxane (3 mL) and water (1.5 mL) were added, and the mixture was stirred at 80-95 C. for 1 to 4 h. After cooling to rt, the mixture was poured into EtOAc/H2O (1:1, 10 mL) and the aqueous layer was extracted with EtOAc (5 mL×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (EtOAc/heptanes) afforded the desired biaryl product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1049744-89-9, 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. 1049744-89-9, name is 2-Hydrazino-5-(trifluoromethyl)pyridine, HCl. A new synthetic method of this compound is introduced below.

(2) Subsequently, Journal of Chemical Society Perkin Trans I (J. Chem. Soc. Perkin trans. I), p. 1875 (in 1988), it gave way to Ethoxy methylene ethyl acetoacetate (6.1g) and the above-described 5- (2-trifluoromethyl synthesized as described in the methyl) pyridin-2-yl hydrazine hydrochloride (7.0g ) water (40), ethanol (40) was added to a solvent mixture, and addition of sodium hydroxide (2.6g), the reaction mixture was stirred for 3 hours at reflux temperature and further stirred for one hour. The reaction solution was treated with a 1N aqueous hydrochloric acid solution, and by purifying the precipitated solid with ethyl acetate-hexane mixed solvent -n- 5-methyl-1- [5- (trifluoromethyl) pyridin-2-yl] -1H- pyrazol to give the 4-carboxylic acid (6.5g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1049744-89-9, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5, Adding some certain compound to certain chemical reactions, such as: 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine,molecular formula is C6H5BrN2O2, 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 23056-47-5.

Into a 2L 3 -necked round-bottom flask under N2 atmosphere, was placed 2-bromo-4- methyl-5-nitropyridine (100 g, 460.79 mmol, 1 equiv), methyl 2,2-difluoro-2- (fluorosulfonyl)acetate (177.0 g, 921.57 mmol, 2 equiv), and Cul (70.2 g, 368.60 mmol, 0.800 equiv) in DMF (1 L). The resulting solution was stirred for 14 h at 120 C and then diluted with NH4CI (3 L), NH4OH (0.5 L). The resulting solution was extracted with ethyl acetate and the combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with petroleum ether to give (40 g, 41.94%) of the title compound as a red oil. GC-MS: (ES, m/z): [M]+ 206.

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. 23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; ASWAD, Fred; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; HATA, Yujiro; SUTTON, JR., James Clifford; (0 pag.)WO2019/236766; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem