Tag: M.W:200-300

Application of 777899-57-7 ,Some common heterocyclic compound, 777899-57-7, 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.

Intermediate 27A: Methyl 2-(1 ,4-diazabicvclo[3.2.2lnonan-4-yl)-5-nitroisonicotinateTo a solution of methyl 2-chloro-5-nitroisonicotinate (Intermediate 26A) (0.1 g, 0.46 mmol) in methanol (3 mL) under nitrogen was added 1 ,4-diazabicyclo[3.2.2]nonane (0.18 g, 0.55 mmol) and triethylamine (7 mg, 0.69 mmol), reaction then stirred overnight. The reaction mixture was concentrated and purified by a 10g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-(1 ,4-diazabicyclo[3.2.2]nonan-4-yl)-5- nitroisonicotinate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,777899-57-7, its application will become more common.

Reference:
Patent; N.V. ORGANON; RATCLIFFE, Paul David; CLARKSON, Thomas Russell; JEREMIAH, Fiona; MACLEAN, John Kinnaird Ferguson; WO2011/45258; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1261269-66-2, 2,4,6-Trichloronicotinaldehyde, 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, 1261269-66-2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H2Cl3NO

Ethylhydrazine (2.16 g, 14.39 mmol, 1.00 equiv) was added to a solution of2,4,6-trichloropyridine-3-carbaldehyde (3 g, 14.26 mmol, 1.00 equiv) and triethylamine (4.3 g,42.49 mmol, 3.00 equiv) in ethanol (100 mL) at -78C under nitrogen. The resulting solution was stilTed for 3 hours at 0 C. After completion the reaction was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:20) to give the title compound (800 mg, 26%) as a white solid. LC-MS (ES, m/z): 216 [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,1261269-66-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 893423-62-6, 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.893423-62-6, name is tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate, molecular formula is C11H13ClN2O3, molecular weight is 256.69, as common compound, the synthetic route is as follows.

To a solution of tert-butyl (2-chloro-3-formylpyridin-4-yl) carbamate (3-1, 30.5 g, 118.9 mmol) and l-[4-(l,3-dioxolan-2-yl)phenyl]-2-phenylethanone (3-2, 29.0 g, 108.1 mmol) in anhydrousTHF (300 mL) at room temperature was added LHMDS (IM in THF, 248 mL) in a stream. The reaction mixture was stirred at room temperature overnight and then it was refluxed for 24 hr. It was cooled and concentrated to a syrup and treated with NaHCO3 (saturated, 50 mL) and water (300 mL) to form a solid which was collected via filtration. The solid was dried, washed with ether and further dried with toluene azeotropically to give the title compound. LRMS m/z (M+1) Calcd: 389.1, found 389.1.

Statistics shows that 893423-62-6 is playing an increasingly important role. we look forward to future research findings about tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885276-93-7, Adding some certain compound to certain chemical reactions, such as: 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate,molecular formula is C10H9BrN2O2, 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 885276-93-7.

Synthesis of Exemplary CompoundsSynthesis of ethyl 5-{{2R,4S)-4-fluoro-2-(3-fluoroDhenyl)Dyrrolidin-1-yl)Dyrazolo[1 ,5- -3-carboxylate (X- 1)[000300] A N2 purged flask was charged with ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3- carboxylate (27 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 2 muiotaetaomicronIota), xantphos (5 mg, 8 muiotaetaomicronIota), cesium carbonate (46 mg, 0.14 mmol), 1 ,4-dioxane (0.5 ml_) and (2R,4S)-4-fluoro-2-(3-fluorophenyl)pyrrolidine (1-6) (18 mg, 0.1 mmol). The contents were heated to 120 C for 12 hours. Upon cooling to room temperature the reaction was partitioned with EtOAc and water. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by column chromatography on silica gel withEtOAc/hexanes gradient as eluant to yield ethyl 5-((2R,4S)-4-fluoro-2-(3- fluorophenyl)pyrrolidin-1 -yl)pyrazolo[1 ,5-a]pyridine-3-carboxylate (X-1 ). 1 H NMR (400MHz, CDCI3) delta 8.20 (s, 1 H), 8.16 (d, J = 7.6 Hz, 1 H), 7.31 (td, J = 5.6, 7.6 Hz, 1 H), 7.05 (d, J = 7.6 Hz, 1 H), 6.98 (d, J = 2.8 Hz, 1 H), 6.96 – 6.91 (m, 2 H), 6.24 (dd, J = 2.8, 8.0 Hz, 1 H), 5.39 (d, J = 52.8 Hz, 1 H), 5.04 (dd, J = 7.2, 9.2 Hz, 1 H), 4.34 – 4.26 (m, 2 H), 4.17 – 3.90 (m, 2 H), 2.93 – 2.81 (m, 1 H), 2.1 1 (dddd, J = 3.6, 9.2, 13.2, 40.8 Hz, 1 H). MS m/z 372.1 (M+1 )+.

According to the analysis of related databases, 885276-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-02-2, 5-Bromo-4-methylpyridine-2-carboxylic 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, COA of Formula: C7H6BrNO2, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO2

Step 1: [0420] To a solution of 5-bromo-4-methylpicolinic acid (400 mg, 1.85 mmol) in dry THF (3 mL) was added borane THF complex (1M in THF, 7.4 mL, 7.4 mmol) at 0° C. and the mixture was stirred at RT overnight. The mixture was cooled to 0° C. and aqueous NH4Cl was added. The mixture was extracted with EtOAc, the combined organic layers were dried and the volatiles were removed under reduced pressure (308 mg, 82percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-02-2, 5-Bromo-4-methylpyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214377-42-0, Adding some certain compound to certain chemical reactions, such as: 1214377-42-0, name is 5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine,molecular formula is C7H5BrF3NO, 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 1214377-42-0.

3-[6-(6-Methoxy-5-trifluoromethyl-pyridin-3-yl)-5, 6, 7, 8-tetrahydro-pyrido[4, 3-d]pyrimidin-4- yloxy]-azetidine-1 -carboxylic acid tert-butyl ester; To a glass vial was added 3-(5,6J,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-azetidine-1- carboxylic acid tert-butyl ester (1 10 mg, 0.359 mmol), 5-Bromo-2-methoxy-3-(trifluoromethyl)pyridine (92 mg, 0.359 mmol), cesium carbonate (234 mg, 0.718 mmol), tris(dibenzylideneacetone)dipalladium(0) (33 mg, 0.036 mmol), X-Phos (58 mg, 0.122 mmol) and anhydrous dioxane (2.0 mL). The vial was flushed with a stream of argon for 15 sec and capped. The mixture was heated with stirring for 1 .5h at 1 10C and then stirred at room temperature for 18h. Diluted with CH2CI2 (50 mL), filtered through a celite pad and concentrated in vacuo. Purified by reverse phase Gilson HPLC (Method A) to give the 3-[6- (6-methoxy-5-trifluoromethyl-pyridin-3-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy]- azetidine-1 -carboxylic acid tert-butyl ester trifluoroacetate as a brown gum (186 mg, 87% yield) LCMS: [M+H]+=482.3, Rt (7)= 1.56 min.

According to the analysis of related databases, 1214377-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 215364-85-5, 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. 215364-85-5, name is 3-Bromo-2-chloropyridin-4-amine, molecular formula is C5H4BrClN2, 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 stirred solution of 3-bromo-2-chloropyridin-4-amine (5.00 g, 24.10 mmol) in concentrated H2S04 (36 mL) at 5 C was added KNO3 (4.87 g, 48.20 mmol). The resultant solution was allowed to warm to room temperature and stir for overnight. The reaction mixture was poured onto ice chips (400 mL) giving a pale yellow precipitate. The precipitate was collected by filtration and washed with water then dried under reduced pressure yield: (5.20 g, 85%). MS [M+H]+= 251.9.

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 215364-85-5, 3-Bromo-2-chloropyridin-4-amine.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; REJ, Rohan; (76 pag.)WO2019/222069; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86447-11-2, 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. 86447-11-2, name is 1-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

22.7 g of N-Boc-1,2,3,6-tetrahydropyridine-5-carboxylic acid (0.1 mol) and 120 mL of toluene were added to a 250 mL reaction flask, and 16.6 g (0.1 mol) of bromine was added dropwise at room temperature. After the completion of the addition, the reaction was stirred at room temperature for 30 minutes. After completion of the TLC reaction, 20 mL of sulfolane was added, the temperature was raised to 50-60 C, and 31.2 g (0.4 mol) of pyridine was added dropwise. After the dropwise addition, the bubble is no longer escaped, the temperature to 80-90 reaction 2-3 hours, vacuum distillation 18.1g of colorless liquid N-Boc-1, 2,3,6-tetrahydropyridine-5-bromide in 69% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86447-11-2, 1-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Cangzhou Puri Oriental Technology Co., Ltd; Leng, Yanguo; Yu, Weidong; Zhang, Jin; (6 pag.)CN105503924; (2016); 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. 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5ClN2O4

11231] To a solution of 643-1 (1.5 g, 6.9 mmol) in DMF (20 mL) was added 2- benzyloxyl ethanol (6.3 g, 41 mmol) at 25 °C. The solution wras stirred for 6 h and then poured into 0 (20 mL). The mixture was extracted with EA (2 x 40 mL). The combined organic phase was washed with brine, dried over anhydrous Na^SC^ and concentrated under reduced pressure. The residue was purified by column chromatography using 5-10percent EA in PE as the eluent to give a mixture of 643-2 and 643-2 A ( 1 .50 g).

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

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 187242-88-2, 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. 187242-88-2, name is 2-Chloro-3-nitro-6-phenylpyridine. A new synthetic method of this compound is introduced below.

1? (48.0 g, 1.0 equiv.), 2? (59.0 g, 1.1 equiv.), and Na2CO3 (43.4 g, 2.0 equiv.) were charged to a 2 L, 3-neck flask. DMA (310 mL, 6.5 vol.) was added and the reaction was heated to 100 C. After 18.5 hours, HPLC analysis showed the reaction to be complete. The reaction was cooled to 9 C. and 2-MeTHF (960 mL, 20 vol.) was added. 10% aqueous solution of NaCl (720 mL, 15 vol.) was added resulting in some solid formation. The mixture was stirred for one hour and then transferred to a separatory funnel (rinsed the solids forward with 100 mL water). The layers were separated and the aqueous layer (Vaq1200 mL) was back extracted with 2-MeTHF (2×200 mL). The combined organics were then washed with 10% aqueous solution of NaCl (2×250 mL) and then analyzed by 1H NMR for DMA (0.3 wt %). After holding the solution overnight, an aliquot was taken out (6 mL) and was washed (3 mL) with water which resulted in a nice phase split (took >30 minutes). Water (650 mL, batch size) was added and stirred for 10 minutes and then transferred to a separatory funnel and allowed to sit. After 90 minutes, a partial phase split was realized (Vaq=250 mL). Brine (250 mL) was added resulting in a phase split. The organic layer (1300 mL, 27 vol., Kf=3.45%) was split off and charged to a 3-L RB flask. The flask was heated (atmospheric) to distill off some of the 2-MeTHF. Once 15 volumes of 2-MeTHF (720 mL) remained (30 minutes), the solution was reanalyzed for water content (Kf=0.24%). The reaction was then cooled to 50-55 C. and polished filtered through filter paper (very little solids present). The solution was then recharged to the 3-L flask (after cleaning flask) and the solution was distilled down to 9 volumes (430 mL). The solution was then heated to 70 C. and heptane was added in portions over one hour. The heat was then turned off and the solution was allowed to slowly cool to room temperature (after one hour the temperature was 48 C.). After stirring for 70 hours, the mother liquor was checked by HPLC analysis for 3 (2.7 mg/mL) and then filtered. The solids were washed with a 25% 2-MeTHF/heptane solution (75 mL, slurry) followed by 2×240 mL displacement wash with the same solution. The cake was washed one more time with heptane (240 mL) and then dried in a vacuum oven for 20 hours at room temperature. 3 (81.1 g, 86% yield, 99.2% AUC) was isolated as a dark red solid. 1H NMR (CDCl3) analysis showed no residual solvent present.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187242-88-2, 2-Chloro-3-nitro-6-phenylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; Bates, Craig; Chen, Jian-Xie; Mao, Jianmin; Reed, David P.; US2015/266876; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem