Tag: M.W:200-300

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. 69722-29-8, name is Ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, molecular formula is C11H12N4O2, 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. SDS of cas: 69722-29-8

Reference Example 2-64 1-(2-Pyridinyl)-1H-pyrazol-5-ylamine A suspension of ethyl 5-amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate (27.9 g, 120 mmol) in 4N sodium hydroxide (300 mL) was heated under reflux for 1 hour. The suspension was allowed to cool to room temperature, neutralized by the addition of conc. hydrochloric acid, and further made acidic by the addition of acetic acid. The resulting crystals were collected by filtration, washed with ethanol, and air dried. The crystals thus obtained were subjected to heat at 200 C., and washed with diethylether to give the title compound (6.02 g, 31% yield). NMR (CDCl3) delta: 5.51 (1H, d, J=1.8 Hz), 5.95 (2H, br s), 7.07-7.13 (1H, m), 7.42 (1H, d, J=1.8 Hz), 7.75-7.84 (1H, m), 7.98 (1H, d, J=8.4 Hz), 8.33 (1H, dd, J=1.6 Hz, 4.6 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 69722-29-8.

Reference:
Patent; Uchikawa, Osamu; Mitsui, Keita; Asakawa, Akiko; Morimoto, Shigeru; Yamamoto, Masataka; Kimura, Hiroyuki; Moriya, Takeo; Mizuno, Masahiro; US2003/187014; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 590371-58-7, 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. 590371-58-7, name is 3-Bromo-2-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-2-(trifluoromethyl)pyridine (1.0 g, 4.42 mmol), XantPhos (256 mg, 0.442 mmol), Pd2(dba)3 (203 mg, 0.221 mmol) in dioxane (12 mL) was added (at RT and under N2) 2-ethylhexyl-3-mercaptopropanoate (1.1 mL, 4.87 mmol) followed by addition of DIPEA (1.55 mL, 8.85 mmol). The resulting solution was stirred in a microwave reactor for 1 h at 110 C. After cooling to RT, the reaction was filtered through a pad of Celite followed by EtOAc (25 mL) wash. The combined filtrates were concentrated and the resulting residue was purified by silica chromatography (0 to 30% gradient of EtO Ac/heptane) to give 2-ethylhexyl 3-((2-(trifluoromethyl)pyridin-3-yl)thio)propanoate (1.41 g, 3.88 mmol). MS m/z 364.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,590371-58-7, 3-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; CHEN, Christine Hiu-tung; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KARKI, Rajesh; KATO, Mitsunori; LAMARCHE, Matthew J.; PEREZ, Lawrence Blas; SMITH, Troy Douglas; WILLIAMS, Sarah; GIRALDES, John William; TOURE, Bakary-barry; SENDZIK, Martin; WO2015/107495; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1134327-98-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1134327-98-2, name is Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 7-Bromoimidazo[1 ,2-a]pyridine-3-carboxylicEthyl 7-bromoimidazo[1 ,2-a]pyridine-3-carboxylate (step 2)(30.81 g, 1 14 mmol) in MeOH (172 ml) was treated with 2M NaOH (172 ml, 343 mmol) and the mixture was heated to 60C for 40 minutes. The volatile solvent was removed in vacuo and the crude material was treated with 2M sodium bisulfate solution to adjust the pH to 6-7. The resulting solid was collected by filtrationand added to water (400 ml). The mixture was stirred and heated to 90C for 1 h. After cooling to RT, the suspension was filtered and dried in a vacuum over at 40C to afford the title product;LC-MS: Rt 0.59 mins; MS m/z 243.1 {M+H}+; Method 2minl_C_v003

According to the analysis of related databases, 1134327-98-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; IRM LLC; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon Christopher; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; SVIRIDENKO, Lilya; THOMSON, Christopher; YEH, Vince; JANUS, Diana; WEST, Ryan; WO2013/30802; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139042-59-4, 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.139042-59-4, name is 5-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.

A mixture of compound J-1 (25 g, 125.6 mmol), NBS (24.5 g, 138.2 mmol) and p-TSA (3.4 g, 20.9 mmol) wasstirred at 100 C under N2 for 2 hours. The mixture was then cooled to rt and dissolved in DCM. The resulting mixturewas quenched with water and extracted with DCM (50 mL x 3). The combined organic phases were dried over anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) =5/1) to give the title compound J-2 (25 g, 71%). The compound was characterized by the following spectroscopic data:MS-ESI: m/z 279.9 [M+H]+; and1H NMR (400 MHz, CDCl3): delta 8.95 (d, J = 1.12 Hz, 1H), 8.11-8.14 (m, 1H), 7.66-7.68 (m, 1H), 4.41 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 139042-59-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 630120-99-9, 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.630120-99-9, name is 5-(Benzyloxy)-2-bromopyridine, molecular formula is C12H10BrNO, molecular weight is 264.1179, as common compound, the synthetic route is as follows.

To a solution of 5-(benzyloxy)-2-bromopyridine (200 mg, 0.757 mmol), methanamine (70.6 mg, 2.272 mmol) and sodium 2-methylpropan-2-olate (437 mg, 4.54 mmol) in THF (5 mL) was added Pd2dba3 (69.3 mg, 0.076 mmol) and dicyclohexyl(2?,4?,6?-triisopropyl-[1,1?-biphenyl]-2-yl)phosphine (36.1 mg, 0.076 mmol). The reaction mixture was stirred at 60 C. for 15 h. The mixture was cooled and diluted with water (10 mL). After the mixture was extracted with EtOAc (10 mL×3), the combined organic fractions were washed with water (20 mL×3), dried (anhydrous Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (1/1 petroleum ether/EtOAc) to give the title compound. MS: 215 (M+1).

Statistics shows that 630120-99-9 is playing an increasingly important role. we look forward to future research findings about 5-(Benzyloxy)-2-bromopyridine.

Reference:
Patent; BAO, JIANMING; GAO, XIAOLEI; KNOWLES, SANDRA L.; LI, I, CHUNSING; LO, MICHAEL MAN-CHU; MAZZOLA, Jr., ROBERT D.; ONDEYKA, DEBRA L.; STAMFORD, ANDREW W.; ZHANG, FENGQI; (214 pag.)US2017/183342; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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.1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, molecular weight is 232.0314, as common compound, the synthetic route is as follows.

To a solution of 5-bromo-6-methoxy picolinicacid1 (1.5 g, 0.00646 mol) in DMF (15mL, 10 vol), cooledto 0oC Na2CO3 (685 mg, 0.00646 mol) and MeI (0.834 mL,0.0129 mol) were added and the mixture was stirred for 16hat room temperature. Water was added, extracted with ethylacetate, concentrated under reduced pressure to obtain 5-bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester(1.5 g, 0.00609 mol) in EtOH (15mL), NH2NH2.H2O (1.21 g,0.0243 mol) was added and the mixture was stirred for 3h at70oC, cooled to room temperature, solvents were evaporated,water (15mL) was added, filtered the reaction mass, to givepure compound 2.

Statistics shows that 1214334-70-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-6-methoxypicolinic acid.

Reference:
Article; Namani, Vasu; Goud, B. Bharath Kumar; Kumari, Y. Bharathi; Kumbham, Ramesh; Letters in Organic Chemistry; vol. 13; 4; (2016); p. 249 – 254;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1188477-11-3, 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. 1188477-11-3, name is tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl ((5-bromopyridin-2-yl)methyl)carbamate (2.2 g, 7.7 mmol) in 1,4-dioxone (4 mL) was added a solution of HCl in 1,4-dioxane (20 mL, 60 mmol, 3 M HCl in 1,4-dioxane). The mixture was stirred at 28C for 2 hr then concentrated to dryness to give the crude product (2.2 g crude) as yellow solid which was directly used in the next step without further purification. LC-MS: m/z 186,188 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1188477-11-3, tert-Butyl ((5-bromopyridin-2-yl)methyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 35905-85-2, 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. 35905-85-2, name is 2-Bromonicotinic acid. A new synthetic method of this compound is introduced below.

Step 2: Methyl 2-bromonicotinate (G2); A solution of of CH2N2 (4 eq.) in Et2O (1 M) was added dropwise to a solution of 2- bromonicotinic acid in THF (0.5 M) at RT. The reaction mixture was stirred at room temperature overnight, then quenched by dropwise addition of AcOH (4 eq.). The organic phase was washed with water and brine and dried (MgSO4). Evaporation of the solvent yielded (75%) the title compound which was used in the next step without further purification. 1H NMR (300MHz, CDCl3, 300K) delta 8.47 (IH, dd, J= 4.8 Hz, 2.1 Hz), 8.07 (IH, dd, J= 7.8 Hz, 2.1 Hz), 7.35 (IH, dd, J= 7.5 Hz, 4.5 Hz), 3.93 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,35905-85-2, 2-Bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/112832; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-14-2, 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. 83004-14-2, name is 2-Bromo-4-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 59 A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (950 mg, 3 mmol), (prepared as described for the starting material in Example 24), 2-bromo-4-bromomethylpyridine (765 mg, 3 mmol) and potassium carbonate (2.38 g 17 mmol) in DMF (10 ml) was heated at 80 C. for 2 hours. The mixture was allowed to cool, poured into water and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent removed by evaporation and azeotroped with toluene. The residue was triturated with ethyl acetate/hexane and the solid product collected by filtration, washed with ethyl acetate/hexane and dried to give 7-((2-bromo-4-pyridyl)methoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (647 mg, 44%). m.p. 210-212 C. 1 H NMR Spectrum: (DMSOd6) 3.98(s, 3H); 5.40(s, 2H); 7.25(s, 1H); 7.30(d, 1H); 7.50(s, 1H); 7.50(d, 1H); 7.55(m, 2H); 7.74(s, 1H); 7.86(s, 1H); 8.35(br s, 1H); 8.42(d, 1H); 9.56(s, 1H) MS – ESI: 489 [MH]+ Elemental analysis: Found C 52.0 H 3.2 N 11.2 C21 H15 N4 O2 BrClF Requires C 51.5 H 3.1 N 11.4%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83004-14-2, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 754230-78-9 ,Some common heterocyclic compound, 754230-78-9, molecular formula is C12H11BrN2O, 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.

Example 85A Ethyl 8-(benzyloxy)-6-bromo-2-methylimidazo[1,2-a]pyridine-3-carboxylate Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine Example 84A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g 3 A molecular sieve were suspended in 6 l of ethanol and boiled at reflux for 72 h. The reaction mixture was filtered off through kieselguhr and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate 9:1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound. LC-MS (Method 17): Rt=1.31 min MS (ESpos): m/z=389 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,754230-78-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem