Tag: M.W:200-300

Related Products of 20511-12-0, Adding some certain compound to certain chemical reactions, such as: 20511-12-0, name is 5-Iodopyridin-2-amine,molecular formula is C5H5IN2, 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 20511-12-0.

Step 13-Bromo-5-iodopyridin-2-amine Procedure:To a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 mL) was added NBS (20.2 g, 113 mmol) slowly at room temperature. After the addition, the reaction mixture was stirred at room temperature for a further 72 h. The solvent was evaporated at 40 C. at reduced pressure and the residue was purified by column chromatography (silica gel, 200-300 mesh, ethyl acetate/petroleum ether 3:1, v/v) to give 3-bromo-5-iodopyridin-2-amine (15.9 g, 47%) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 8.07 (s, 1H), 7.98-7.97 (m, 1H), 6.43 (brs, 1H). LC/MS: 298.9 [M+H]+.

According to the analysis of related databases, 20511-12-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/309746; (2012); A1;,
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. 1057682-05-9, name is (R)-6-(3-Methylpiperazin-1-yl)nicotinonitrile, molecular formula is C11H14N4, 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. HPLC of Formula: C11H14N4

To a stirred solution of 3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoic acid (5.0 g, 21.19mmol, obtained from Example 29, step 3) in dry DMF (40 mL, -8 vol), 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile ( 4.06 g, 20 mmol), EDClHCl (6.08 g, 31.6 mmol),HOBt (3.43 g, 25.4 mmol) and DIPEA (14.5 mL, 84.5 mol) were added at 10-15C andstirred for 22 h. The reaction mixture was quenched with ice cold water (500 mL) andextracted with EtOAc (3 x 70 mL). The combined organic layers were dried over anhydrousNa2S04 and concentrated under reduced pressure to get crude compound. Crude compoundwas stirred with EtOAc (50 mL) for 1 hour at RT, filtered and suck dried. Solid obtained wasagain made slurry with EtOAc. Filtered the solid and washed with EtOAc (50 mL) to afford(50 mL) 6-[(3R)-4-[3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoyl]-3-methyl-piperazin-1-yl]pyridine-3-carbonitrile in 43% yield (3.8g). Chiral HPLC was used to confirm that thecompound is the enantiomer of compound 29. Column used: Lux,5 micron, Cellulose-4 (250X 4.6 mm , 5 micron , Mobile phase: 50:50 n-hexane:(0.1% HCOOH in 1:1ethanol:methanol), Flow rate: 1.0 mL/min, Temperature: 25C. Retention time for Renantiomer= 12.9 min; Retention time for compound 29 = 13.4 min.

With the rapid development of chemical substances, we look forward to future research findings about 1057682-05-9.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 179687-79-7, 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 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 3 Preparation of N-[3-Chloro-4-(2-pyridinylmethoxy)]phenyl-2-cyanoacetamide In a 12-L multi-necked flask, 2-pyridyl carbinol (0.13 kg, 1.19 mole, 1.05 eq) was dissolved in acetonitrile (0.88 L) and to it was added potassium hydroxide flakes (85%) (80 g, 1.25 eq). The resulting suspension was warmed to 35 C. A solution of 3-chloro-4-fluoronitrobenzene (0.20 kg, 1.14 mol) in acetonitrile (1.0 L) was added at 35-40 C. The mixture was held for 18 h until reaction completion. The mixture was then cooled back to 20-25 C., quenched with water (4 L) and the resulting slurry was filtered and washed with water (3×200 mL). The resulting product was isolated as a tan solid (251 g, 84% yield). A mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.149 kg, 0.56 mole) and 2% (w/w) of 5% Pt/C (6.0 g, 50% water wet) in tetrahydrofuran (0.895 L) was hydrogenated in a 2-L stainless steel Parr reactor at 25 psi, 25 C. for a minimum of 8 h. The mixture was filtered through a celite pad (50 g, 15 cm diameter) and washed with tetrahydrofuran (0.45 L). The filtrate was distilled to a volume of 0.30 L and the concentrate was transferred to a 2-L multi-neck flask and used as is in the next step. To the 2-L flask equipped with mechanical stirrer, temperature probe, claisen head and condenser was added ethylcyanoacetate (0.421 kg, 3.72 mole, 6.6 eq.). The reaction mixture was heated to (100-115 C.) while removing tetrahydrofuran and ethanol. The temperature was raised to 125 C. and the mixture was held for a minimum of 24 h until the aniline starting material was consumed and no distillate was collected. The mixture was cooled to room temperature over 1 h. At 50-60 C., solids crystallized out and ethyl acetate (0.15 L) was added. The mixture was further cooled to 0-10 C. and held for 1 h. The mixture was filtered on a 15 cm diameter Buchner funnel and washed with 50 mL of the filtrate followed by pre-cooled (0-10 C.) ethyl acetate (0.15 L). The product was dried at 60 C. for a minimum of 16 h in a vacuum oven to give the titled compound (0.12 kg, 71%) as a brown solid. The product was purified by slurrying in cold ethyl acetate (1-1.3 volumes) for 1 hr. 1H NMR: delta (DMSO-d6) 10.31 (s, 1H, NH), 8.58 (dd, 1H, Ar), 7.86 (dt, 1H, Ar), 7.75 (d, 1H, Ar), 7.55 (d, 1H, Ar), 7.39-7.32 (m, 2H, Ar), 7.21 (d, 1H, Ar), 5.25 (s, 2H, OCH2Pyr), 3.88 (s, 2H, NCCH2CO).

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 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine.

Reference:
Patent; Chew, Warren; Papamichelakis, Maria; US2006/270669; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1044872-40-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1044872-40-3 as follows.

To a solution of methyl 2-amino-4,6-dichloro-pyridine-3-carboxylate (300 mg, 1.357 mmol) in dry THF (7 mL) was added a 3M solution of methylmagnesium bromide in diethyl ether (1.58 mL, 4.75 mmol) dropwise under nitrogen at -60 C. The reaction mixture was stirred at -60 C to 0 C for 1 h. The progress of reaction was monitored by TLC & 1H NMR. After completion of reaction, the mixture was quenched using aqueous saturated solution of ammonium chloride and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography on silica (100:200 mesh) using 10% EtOAc-hexane system as eluent to afford 2-(2-amino-4,6-dichloro-3-pyridyl)propan- 2-ol (263 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1044872-40-3, its application will become more common.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 821791-58-6, Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate, 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, 821791-58-6, blongs to pyridine-derivatives compound. HPLC of Formula: C9H10ClNO3

4-CHLORO-1-METHYL-6-OXO-1, 6-DIHYDRO-PYRIDINE-3-CARBOXYLIC acid ethyl ester (2.65 g, 12.3 MMOL) was dissolved in a mixture of tetrahydrofuran (16 mL), acetonitrile (16 mL) and water (8 mL). Sodium hydroxide (1.23 g, 30.8 MMOL) was added and the reaction mixture was allowed to stir at ambient temperature for 24 h. The reaction mixture was diluted with water (50 mL) and was acidified to pH 2 with 1 M hydrochloric acid and was extracted many times with ethyl acetate (about 1 L). The extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to afford an orange-tinged solid. Crystallization from methanol-ethyl acetate afforded 4-CHLORO-1-METHYL-6-OXO-1, 6-DIHYDRO-PYRIDINE-3-CARBOXYLIC acid (0.859 g, 37 % yield) as an off-white solid :’H NMR (DMSO-D6, 400 MHz) 8 13.02 (br s, 1 H), 8.58 (s, 1 H), 6.58 (s, 1 H), 3.48 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,821791-58-6, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/818; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, 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, Formula: C12H9ClN2O3, blongs to pyridine-derivatives compound. Formula: C12H9ClN2O3

Step 2: 3-chloro-4-(pyridin-2-ylmethoxy)aniline The 2-((2-chloro-4-nitrophenoxy)methyl)pyridine (3.9 g, 15 mmol), zinc powder (5.8 g, 88 mmol) and ammonium chloride (2.4 g, 44 mmol) were added into a mixed solution of ethanol (60 mL) and H2O (10 mL). The mixture was stirred at 60 C. overnight. Then the reaction mixture was poured into 200 mL of H2O, extracted with ethyl acetate. The organic phase was separated, washed with saturated brine and dried. The solvent was removed in vacuo, and the compound shown in the title (3.4 g, 98%) was obtained. 1H NMR (CDCl3): delta 8.57 (1H, d, J=4.8 Hz), 7.75-7.70 (1H, m), 7.65-7.63 (1H, m), 7.23-7.20 (1H, m), 6.81 (1H, d, J=9.2 Hz), 6.77 (1H, d, J=2.8 Hz), 5.18 (2H, s), 3.48 (2H, br).

The synthetic route of 179687-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; CENTAURUS BIOPHARMA CO., LTD.; LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD.; XIAO, Dengming; ZHU, Yan; HU, Yuandong; WANG, Huting; LI, Jijun; PENG, Yong; ZHANG, Hui; LUO, Hong; KONG, Fansheng; HAN, Yongxin; (25 pag.)US2016/214964; (2016); A1;,
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. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-bromo-6-methylnicotinate

To a stirred solution of methyl 2-bromo-6-methylnicotinate (US2010144760, 2.79 g, 12.1 1 mmol) in acetonitrile (50 ml) (degassed by N2 purge separately) was added bis(triphenylphosphine)palladium(II) chloride (1.063 g, 1.514 mmol). The reaction mixture was heated up to 70 C and diisopropyl ethyl amine (7.83 g, 60.6 mmol) was added slowly, followed by a solution of (R)-4-(4-(3-ethynylcyclopent-2- en- l-yl)piperazin- l-yl)benzonitrile (Compound lj, 2.8 g, 10.10 mmol) in acetonitrile (20 ml) was added slowly at the same temperature. The reaction mixture was heated and stirred at 80-85 C for 14 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was distilled under vaccum to dryness to obtain a crude product which was purified by column chromatography over silica gel (100-200 mesh) using 60-80% ethyl acetate in hexane as an eluent to obtain the title product (0.9 gm, 20.90 % yield). iH NMR (400 MHz, CDC13) delta 8.17 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.2 Hz, 1H), 6.90 – 6.87 (m, 2H), 6.36 (d, J = 2.3 Hz, 1H), 4.08 – 4.03 (m, 1H), 3.96 (s, 3H), 3.40 – 3.35 (m, 4H), 2.75 – 2.67 (m, 6H), 2.64 (s, 3H), 2.13 – 2.09 (m, 1H), 2.03 – 1.95 (m, 1H). MS: m/z 427.24 (M+l).

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, 885277-48-5, Methyl 2-bromo-6-methylnicotinate.

Reference:
Patent; LUPIN LIMITED; KARCHE, Navnath, Popat; TILEKAR, Ajay, Ramchandra; KURHADE, Sanjay, Pralhad; JADHAV, Ganesh, Rajaram; GUPTA, Nishant, Ramniwasji; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (191 pag.)WO2017/29601; (2017); A1;,
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. 144584-32-7, name is 3-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, 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. Recommanded Product: 3-Bromo-2,4-dichloropyridine

A. Preparation of 1-(3-bromo-4-chloropyridin-2-yl)hydrazine To stirring anhydrous dioxane (30 mL) at room temperature was added anhydrous hydrazine (3.29 mL, 105 mmol), followed by portion-wise addition of solid 3-bromo-2,4-dichloropyridine (2.39 g, 10.53 mmol, prepared as described in M. A. Walters, et al., Synth. Comm., Vol. 22, pp. 2829-2837, 1992). The resulting turbid solution was stirred in a 65 C. oil bath for 2 h. After cooling to room temperature, the reaction mixture was evaporated to dryness under reduced pressure. The resulting residue was triturated with isopropanol (50 mL), in which it was only partially soluble, and the mixture was filtered, collecting the solid. The filtrate was evaporated, and the resulting solid was triturated once again with isopropanol (25 mL) and filtered, collecting the solid. The two crops of solid were combined and dried in a 50 C. vacuum oven to obtain 1.438 g of an off-white solid, which contained about 70% of the title compound 1-(3-bromo-4-chloropyridin-2-yl)hydrazine and about 30% of its regioisomer (1-(3-bromo-2-chloropyridin-4-yl)hydrazine). HPLC/MS: retention time=1.06 min, [M+H]+=221.

With the rapid development of chemical substances, we look forward to future research findings about 144584-32-7.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1070892-04-4, 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. 1070892-04-4, name is 5-Bromo-2-(trifluoromethyl)isonicotinonitrile, molecular formula is C7H2BrF3N2, 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.

A mixture of 4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-5- (4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzenesulfonamide (150 mg, 0.34 mmol), 5-bromo-2-trifluoromethyl-isonicotinonitrile (111 mg, 0.44 mmol), Pd(Ph3P)4 (40 mg, 0.034 mmol) and Na2CO3 (217 mg, 2.1 mmol) in dioxane (2 ml.) and water (0.2 mL) was degassed with N2 for 5 min. The reaction vessel was sealed and then heated at 90 0C for 16 hrs. The mixture was absorbed onto silica gel and purified by chromatography on silica gel eluting with 20-25% acetone in hexanes to give 4-chloro- 5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl- benzenesulfonamide as an oil (69 mg). A small sample was also purified by prep. LCMS. MS: 541.1 (M+H)+; tR = 7.59 min (method 2).

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 1070892-04-4, 5-Bromo-2-(trifluoromethyl)isonicotinonitrile.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156094-63-2 , The common heterocyclic compound, 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, 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.

General procedure: To a flame-dried flask containing z-BuOK (1.10 equiv.) and anhydrous DMF (2.5 mL/mmol) was added ethyl 2-((diphenylmethylene)amino)acetate (1.05 eq. ) at 0 C under argon. After 10 min, arylmethyl bromide (1.0 eq.) was added. The resulting reaction mixture was stirred at 0 C for 10 min and was allowed to warm up to 4 C and stirred at 4 C overnight. The reaction mixture was then slowly poured into water, extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure to evaporate the DCM solvent. The residue was then treated with a mixture of EtOH/concentrated HC1 (25:1 v/v). The resulting solution was stirred at room temperature for 2 h. Upon the evaporation of EtOH and most of the DMF, the residue was basified by 2 N K2CO3 solution to pH > 10 and extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure. The residue was purified through flash chromatography on silica gel (1: 19 CH3OH/CH2CI2) to afford the desired ethyl 2-amino-3- arylpropanoate product as a colorless gel.

The synthetic route of 156094-63-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DE BRABANDER, Jef; ROSENBAUM, Daniel; LIANG, Qiren; WANG, Wentian; (343 pag.)WO2019/191327; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem