Tag: M.W:200-300

Electric Literature of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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.

To a solution of 5-bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 C, was added oxalyl dichloride (16.98 mL,194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reaction mixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm) Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; HOUSE, David; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (141 pag.)WO2017/50714; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 61338-13-4, 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic 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, 61338-13-4, blongs to pyridine-derivatives compound. Safety of 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic acid

To a 1000 ml three-necked flask, 600 ml of tetrahydrofuran, 2- (4-methyl-2-phenyl-1-piperazinyl)(134 g, 0.45 mol),Zinc chloride (306 g, 2.25 mol) was added sodium borohydride (85 g, 2.25 mol) in portions carefully. The temperature was raised to 60-85 C after addition and reflux with stirring for 16 hours, cooled to 0 C and carefully quenched with methanol The reaction mixture was removed under reduced pressure. 600 ml of 6N hydrochloric acid was added and the mixture was heated to 80 C with heating and stirred for 1 hour. The mixture was cooled to room temperature and extracted with methylene chloride (2 L × 3). The organic phase was dried over 1 kg of anhydrous sodium sulfate, A white solid was obtained. The white solid was further dried by blowing with air at 50 C to give 113 g of 1-(3-hydroxymethylpyridin-2-yl) -4-methyl-2-phenylpiperazine as a white solid in 89% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61338-13-4, its application will become more common.

Reference:
Patent; Beijing Ha Sanlian Science And Technology Co., Ltd.; Harbin Sanlian Pharmaceutical Co., Ltd.; Liu Jinai; Li Yuanzhen; Ning Ruibo; Wang Mingxin; (8 pag.)CN105367571; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 63897-12-1, 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. 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine, 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.

EXAMPLE 238 3-Amino-2,4-bis(methylthio)-6-methylpyridine To a solution of 15.5 g (0.22 mol) sodium methanethiolate in 200 ml methanol was added slowly with stirring under nitrogen a solution of 20.8 g (0.1 mol) 3-nitro-2,4-dichloro-6-methylpyridine in 150 ml methanol. A precipitate formed and the mixture was stirred overnight at room temperature. The mixture was then filtered and the solid was washed first with methanol and then with water. 3-Nitro-2,4-bis(methylthio)-6-methylpyridine (18.9 g, 82% yield) was obtained as a yellow solid, mp 172-176 C. 1 H NMR (CDCl3): delta 2.45 (s, 3H); 2.51 (s, 3H); 2.55 (s, 3H); 6.77 (s, 1H).

According to the analysis of related databases, 63897-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US5362878; (1994); A;,
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. 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-5-chloropyridin-2-amine

Step 2: tert-Butyl 4-(6-(6-amino-3-chloropyridin-2-yl)-5-chloro-7-fluorobenzo[c]isothiazol-3-yl)piperazine-1-carboxylate A mixture of tert-butyl 4-(5-chloro-7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c]isothiazol-3-yl)piperazine-1-carboxylate (99.5 mg, 0.200 mmol), SPhos Pd G3 (17.3 mg, 0.020 mmol), 6-bromo-5-chloropyridin-2-amine (Combi-blocks Inc., San Diego, Calif., USA, 124 mg, 0.6 mmol), sodium carbonate (85 mg, 0.80 mmol) in water (0.25 mL), and 1,2-DCE (0.75 mL) was heated at 50 C. for 2 h. The reaction mixture was concentrated in vacuo and chromatographically purified (silica gel, 0% to 100% (3:1) EtOAc-EtOH in heptane) to give tert-butyl 4-(6-(6-amino-3-chloropyridin-2-yl)-5-chloro-7-fluorobenzo[c]isothiazol-3-yl)piperazine-1-carboxylate: m/z (ESI, +ve) 498.0 (M+H)+.

The synthetic route of 1004294-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19755-53-4, 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. 19755-53-4, name is 2-Bromo-3-nitropyridine. A new synthetic method of this compound is introduced below.

2. N-(4-TERT-BUTYL-PHENYL)-4- (3-NITRO-PYRIDIN-2-YL)-BERAZAMIDE Bubble nitrogen through a solution of 4-BORONO-N- (4-TERT-BUTYL-PHENYL)-BENZAMIDE (1.3 g, 4.37 mmol), 2-bromo-3-nitro-pyridine (0. 63 g, 3.12 mmol), 2M NA2CO3 (3.9 ml, 2.5 equivalents), in DME for 10 minutes. Add Pd (PPH3) 4 (144 mg) and bubble nitrogen through the solution for two additional minutes. Heat the reaction for 12 hours at 80C. Cool the reaction, concentrate, and partition between EtOAc and water. Dry the solution (Na2SO4) and concentrate under reduced pressure to give the crude product. Purify using chromatography (25% ethyl acetate/hexanes eluent) to give N- (4-tert-butyl-phenyl)-4- (3- nitro-pyridin-2-yl)-benzamide as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19755-53-4, 2-Bromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/56774; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175422-04-5, 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.175422-04-5, name is 2,6-Dibromo-4-nitropyridine, molecular formula is C5H2Br2N2O2, molecular weight is 281.8896, as common compound, the synthetic route is as follows.

To a solution of 99A (0.473 g, 2.66 mmol) in l,4-Dioxane (20 mL) was added DIPEA (1.239 mL, 7.09 mmol) followed by 2,6-dibromo-4-nitropyridine (0.5 g, 1.774 mmol) sealed the tube and heated to 100 C for overnight. The reaction mass was cooled to RT and concentrated under reduced pressure. Purification by flash chromatography gave 101A (brown solid, 0.32 g, 0.842 mmol, 47.5 % yield). LC-MS Anal.Calc?d for CioHnBrFsNsCh 340.99, found [M+H] 342.2 Tr = 3.652 min (Method U).

Statistics shows that 175422-04-5 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-4-nitropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13600-42-5, 2,6-Dichloro-4-(trifluoromethyl)nicotinonitrile, 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, 13600-42-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(1) 11.3 g of 3-cyano-2,6-dichloro-4-trifluoromethylpyridine was gradually added to 22.6 ml of concentrated sulfuric acid, and then the mixture was heated and reacted at 100 C. for one hour. After completion of the reaction, the mixture was poured into ice water, whereupon white precipitates formed. The precipitates were collected by filtration, and the filtrate was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a white solid. This solid and the precipitates previously obtained, were put together to obtain 9.2 g of 2,6-dichloro-4-trifluoromethyl-3-pyridine carboxamide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13600-42-5, its application will become more common.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US5360806; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 106047-17-0, 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.106047-17-0, name is Methyl 4-(pyridin-4-yl)benzoate, molecular formula is C13H11NO2, molecular weight is 213.23, as common compound, the synthetic route is as follows.

Reference Example 18 Methyl 4-[pyridine-N-oxide-4-yl]-benzoate. To a cooled (0 C.) solution of methyl 4-[pyridin-4-yl]-benzoate (2.1 g, 10 mmol) (reference example 19a) in CH2Cl2 (41 mL) is added m-CPBA (3.4 g, 50-60% technical grade, 10 mmol). The resulting solution is stirred for 1 hour then a further portion of m-CPBA added (1.7 g, 5 mmol). This solution is stirred for 1 hour (temperature held between 5-10 C.) then the reaction mixture poured directly onto a silica gel column. Elution with 10% MeOH/40% EtOAc/50% CH2Cl2 gave 2.0 g of the title compound as a tan solid. 1H NMR (CDC3OD) d 3.94 (s, 3H), 7.90 (m, 4H), 8.14 (d, J=8.5 Hz, 2H), 8.39 (d, J=7 Hz, 2H). MS (EI) m/z 230 (M)+.

Statistics shows that 106047-17-0 is playing an increasingly important role. we look forward to future research findings about Methyl 4-(pyridin-4-yl)benzoate.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6541505; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52833-94-0, 2-Amino-5-bromonicotinic 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, name: 2-Amino-5-bromonicotinic acid, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinic acid

Step 2: 5-Bromo-3-(3-(2,2,2-trifluoroethyl)-1 ,2,4-oxadiazol-5-vl)pyridin-2-amine To a stirring suspension of 2-amino-5-bromonicotinic acid (2.3 g, 10.60 mmol) in DCM (53.0 ml), 1-chloro-N,N,2-trimethyl-1-propenylamine (Ghosez’s reagent) (1.683 ml, 12.72 mmol) was added. The reaction mixture was left stirring for 1.5 hours. 3,3,3-trifluoro-N’- hydroxypropanimidamide (step 1) (1.656 g, 11.66 mmol) was then added followed by DIPEA (3.70 ml, 21.20 mmol). The reaction mixture was stirred overnight. T3P (18.56 ml, 31.8 mmol) was added to the mixture and this was microwaved for 3 hours at 100C. The mixture was added to water (100ml) and product extracted into EtOAc (2 x 90ml). The organic extracts were washed with brine, dried over MgS04 and the filtrate was concentrated under reduced pressure. The crude product was purified by adding MeOH (~10ml). The mixture was sonicated and the resulting solid collected by filtration, washed with MeOH and dried to afford the title compound; LCMS: Rt = 1.17 mins; MS m/z 325.0 [M+H]+; Method 2minLowpHv01 1H NMR (400 MHz, DMSO-d6) delta 8.40 (1 H, d), 8.35 (1 H, d), 7.59 (2H, br s), 4.21 (2H, q).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52833-94-0, 2-Amino-5-bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; WO2015/162456; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159503-91-0, 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 159503-91-0, name is tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

2nd step: the metal lithium (1.0g, 0 . 15mol) and double (diisopropylamine) boron bromide (21.8g, 75mmol) by adding 2-methyl tetrahydrofuran (90 ml) in, temperature control -20 C to -10 C, dripping is dissolved in 2-methyl tetrahydrofuran (35 ml) of in N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo (18.9g, 72mmol), stirring after 5 hours, the end of the detection reaction, adding npg (8.6g, 83mmol), heating to reflux reaction. Cooling, adding 10% hydrochloric acid aqueous solution to adjust PH= 5-6, organic layer by adding 10% palladium carbon (1.2g), after the replacement of nitrogen, filled with 1 atmospheric pressure hydrogen, after the reaction, drying of the organic layer, by adding 45 ml normal heptane cooling -10 C pulping, filtering to obtain 14.3g kind of white solid N-Boc-piperidin-4-boronic acid new pentamethylene glycol ester, GC: 98.5%, HNMR: > 98%, yield: 67%.

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 159503-91-0, tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate.

Reference:
Patent; Puri Cangzhou Orient Technology Co., Ltd.; Leng, Yanguo; Feng, Xuemin; Gui, Wenwu; (6 pag.)CN105566368; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem