Month: April 2022

Application of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate, molecular formula is C9H10ClNO2, 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 solution of (E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1, 3, 2] dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol (Example 39-(5); 50.0 mg, 0.10 mmol), (6-chloro-pyridin-3-yl)acetic acid ethyl ester (31.4 mg, 0.15 mmol), tetrakistriphenylphosphine palladium (16.9 mg, 0.0146 mmol) and potassium phosphate (33.4 mg, 0.15 mmol) in N,N-dimethylformamide (0.30 mL) was stirred with microwave heating at 140C for 10 minutes. The reaction mixture was filtered through cotton plug, and the residue was purified by silica gel chromatography (30 to 40% ethyl acetate/hexane) to give the title compound (37.6 mg, 69%). 1H-NMR (chloroform-d): 0.65 (t, 6H, J=7.3Hz), 0.92 (t, 6H, J=7.3Hz), 1.26 (t, 3H, J=7.1Hz), 1.64 (q, 4H, J=7.5Hz), 2.13 (q, 4H, J=7.2Hz), 2.30 (s, 3H), 3.64 (s, 2H), 4.18 (q, 2H, J=7.1Hz), 6.01 (d, 1H, J=16.1Hz), 6.75 (d, 1H, J=16.1Hz), 6.96-6.99 (m, 2H), 7.26-7.32 (m, 3H), 7.68 (s, 2H), 7.85 (d, 2H, J=8.4Hz), 8.56 (s, 1H).

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 197376-47-9, Ethyl 6-Chloropyridine-3-acetate.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79456-33-0, 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.79456-33-0, name is 5-Chloro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.

To a stirred solution of 5-chloro-3-(trifluoromethyl)pyridin-2-amine (Intermediate 47; CAS79456-33-0, 10 g, 50.9 mmol) in aqueous HBr (48 %, 56.7 g, 336 mmol) at -10 C wasadded bromine (23.6 g, 147.5 mmol) dropwise over 20 minutes, followed by a solution ofsodium nitrite (10.2 g, 147.8 mmol) in water (18 mL). The reaction was stirred at ambienttemperature for 2 hours and was basified (pH 9-10) and extracted into diethyl ether. Theorganic was washed with brine, dried (Na2504), filtered and concentrated in vacuo toafford the title compound without further purification.MS ES: 262

The chemical industry reduces the impact on the environment during synthesis 79456-33-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GOLDBY, Anne; JENKINS, Kerry; TEALL, Martin; WO2015/79224; (2015); 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.79055-59-7, name is 2-Bromo-6-methylpyridin-4-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.name: 2-Bromo-6-methylpyridin-4-amine

Lithium bis(trimethylsilyl)amide in THF (4.63 mL, 1 M, 4.63 mmol) was added to ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclobutyl]sulfamoyl]pyrrole-2-carboxylate (492.4 mg, 1.322 mmol) and 2-bromo-6-methylpyridin-4-amine (371.0 mg, 1.98 mmol) in THF (4 mL) and the mixture was stirred for 1 hour. The reaction mixture was quenched with a saturated aqueous NH4CI solution, diluted with brine and extracted with EtOAc. The organic layer was dried over magnesium sulphate, filtered and concentrated. The residue was purified by column (0775) chromatography using a gradient from 10 till 100% EtOAc in heptane. The obtained solid was dissolved in methanol (40 mL) and water was added untill crystallisation began. The product was filtered off and dried overnight in vacuo at 50C resulting in compound 164 (534 mg) as a white powder. Method D: Rt: 1.98 min. m/z: 511.1 (M-H)~ Exact mass: 512.0. DSC: From 30 to 300 C at 10C/min, peak 202.4 C. 1H NMR (400 MHz, ACETONITRILE-d3) delta ppm 1.85 – 1.93 (m, 2 H), 2.36 – 2.46 (m, 5 H), 2.47 – 2.57 (m, 2 H), 3.86 (s, 3 H), 6.48 (br. s, 1 H), 7.25 (d, J=4.8 Hz, 1 H), 7.42 (d, J=1.5 Hz, 1 H), 7.73 (d, J=1.5 Hz, 1 H), 8.47 (br. s, 1 H). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.79 – 1.91 (m, 2 H), 2.27 – 2.38 (m, 2 H), 2.39 – 2.49 (m, 5 H), 3.82 (s, 3 H), 7.52 (d, J=1.3 Hz, 1 H), 7.57 (d, J=4.4 Hz, 1 H), 7.77 (d, J=l . l Hz, 1 H), 8.73 (s, 1 H), 10.46 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,79055-59-7, 2-Bromo-6-methylpyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 696-42-4, 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 696-42-4, name is 5-Fluoronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

[0307] Cesium carbonate (0.734 g, 2.25 mmol) and 5-chloro-3-methylpyridine-2-carbonitrile (0.206 g, 1.35 mmol) wereadded at room temperature to a suspension of the optically active form of cis-1-(diphenylmethyl)-5-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (0.212 g, 0.451 mmol) produced in ReferenceExample 27 in DMSO (2 mL), and the mixture was stirred at 150C for 2 hours. The reaction suspension wascooled to room temperature, then diluted with ethyl acetate, and washed with brine. The obtained organic layer wasdried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residuewas purified by silica gel column chromatography [elute: hexane/ethyl acetate = 92/8 – 50/50 (gradient)] to obtain thetitle compound (0.226 g, yield: 86%, optically active form:_[0327] The title compound (42.7 g, yield: 70%, optically active form) was obtained through reaction at 80C for 1 hourand then at 100C for 5 hours by the method described in Reference Example 30 using 5-fluoropyridine-3-carbonitrile(26.0 mg, 0.213 mmol) instead of 5-chloro-3-methylpyridine-2-carbonitrile.[0328] 1H-NMR (400MHz, CDCl3) delta: 8.46 (1H, d, J=3Hz), 8.25 (1H, d, J=2Hz), 7.43-7.04 (10H, m), 6.91 (1H, s), 6.71(1H, s), 4.56-4.51 (1H, m), 3.96-3.86 (1H, m), 3.83-3.73 (2H, m), 3.72-3.67 (1H, m), 3.02-2.93 (2H, m), 2.87-2.76 (1H,m), 2.08-1.85 (4H, m).

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 696-42-4, 5-Fluoronicotinonitrile.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; ARAI, Masami; KANEKO, Toshio; TERASAKA, Naoki; (95 pag.)EP3081566; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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.

At -78 C., 19.6 ml of 1.9 mol/L solution of hexamethyldisilazane sodium in THF was added dropwise to 100 ml of THF solution containing 2.00 g of 2-(2-chloropyridin-3-yl)acetic acid, and the mixture was stirred for 10 minutes. Next, 1.50 ml of methyl p-fluorobenzoate was added dropwise. The mixture was then brought from -78 C. to room temperature and was stirred for 1 hour. Saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred. Thereafter, ethyl acetate was added, and the resultant liquid mixture was separated. The obtained organic layer was washed with saturated brine and was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography. The title compound was obtained as a colorless amorphous compound weighing 1.45 g. 1H-NMR(CDCl3)delta:8.36(1H,dd,J=4.6,1.9 Hz),8.11-8.07(2H,m),7.62(1H,dd,J=7.4,1.9 Hz),7.27-7.24(1H,m),7.21-7.17(2H,m),4.42(2H,s).

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; FUKUMOTO, Takeshi; NAITO, Ryohei; IKISHIMA, Hideaki; KOUNO, Toshiyuki; NISHIDA, Akihiro; YANAGI, Masanori; KITAJIMA, Kazuki; YUTANI, Satoshi; SHIRAKAWA, Tomomi; OHARA, Toshiaki; (170 pag.)US2019/380340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1079179-12-6 ,Some common heterocyclic compound, 1079179-12-6, molecular formula is C5H2ClFN2O2, 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 2-chloro-3-fluoro-5-nitropyridine (3.0 g, 15.3 mmol) in DMF (30 mL) was added thiomorpholine (1.6 g, 15.3 mmol) and DIEA (5.3 mL, 30.6 mmol). The mixture was stirred at 60C for 16 hours. The reaction was cooled to roomtemperature, and then then was diluted with water (50 mL). The precipitated solid was collected by filtration, and dried to give 4-(3-fluoro-5-nitropyridin-2-yl)thiomorpholine asa solid. ?HNMRoe 8.87 (s, 1H), 7.98 (dd, J= 2.0, 13.6Hz, 1H), 4.15-4.12 (m, 4H), 2.76-2.74 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1079179-12-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YANG, Lihu; OLSEN, David B.; YOUNG, Katherine; SU, Jing; MANDAL, Mihir B.; SUZUKI, Takao; YOU, Lanying; (85 pag.)WO2017/66964; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 185315-53-1 , The common heterocyclic compound, 185315-53-1, name is 3-Chloro-2-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, 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.

Synthesis of 4.5-dichloro-2-((3-chloropyridin-2-vnmethvnpyridazin-3(2HV one (G3-2 32 G3-2 To a solution of compound 4 (200 mg, 1.21 mmol), compound 32 (235 mg, 1.45 mmol) and K2CQ3 (335 mg, 2.42 mmol) in DMF (3 mL) was added KI (20 mg, 0.12 mmol). The solution was stirred at 90 C for 2h. The mixture was cooled to room temperature and quenched with water, extracted with EtOAc for 3 times, combined the organic layer, washed with brine, dried over Na2S(X filtered, concentrated under reduced pressure, purified by HPLC to give G3-2 (126 mg, 42%) as a yellow solid. NMR (DMSO-ifc, 300 MHz): delta 5.53 (s, 2H), 7.38-7.42 (m, 1H), 7.99 (d, J = 8.1 Hz, 1H), 8.27 (s, 1H), 8.41 (d, J = 4.5 Hz, 1H); LCMS [mobile phase: 20-95% Acetonitrile +0.02% NHtOAc] purity is >95%, Rt = 3.365 min; MS Calcd.: 290; MS Found: 291 (M+l)+.

The synthetic route of 185315-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; BECKWITH, Jonathan Roger; DUTTON, Rachel; ESER, Markus; LANDETA, Cristina; BLAZYK, Jessica L.; MEEHAN, Brian M.; HATAHET, Feras; BOYD, Dana; WO2015/143164; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

Potassium bis(trimethylsilyl)amide (25 mL, 12.5 mmol, 0.5M in toluene) was added to a solution of 2-amino-5-bromo-nicotinonitrile (496 mg, 2.5 mmol) in THF (10 mL) at -78 0C which was followed by a dropwise addition of acetyl chloride (533 muL, 7.5 mmol). The reaction was stirred at ambient temperature for 4 h then quenched with ammonium chloride (10 mL, sat). The resulting mixture was extracted with methylene chloride; the organic layer was washed with water and dried over MgSO_j. The volatiles were removed under vacuum to give the title compound (420 mg, 70%). 1H NMR (300 MHz, DMSO-4 delta): 10.92 (s, IH), 8.82 (d, J = 2.3Hz, IH), 8.66 (d, J= 2.3Hz, IH), 2.12 (s, 3H). MS (ESI) m/e: 240 and 242 (M+H)+.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/67416; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62135-58-4, 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. 62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

Under argon atmosphere, ethyl [l,2,4]triazolo[l,5-a]pyridine-2-carboxylate (1 g, 5.23 mmol) was combined with THF (10 mL) at RT to give a brown suspension. Sodium borohydride (1.19 g, 31.4 mmol) was added in four portions. The mixture was heated to 65 C for 15 min. After cooling down to RT, ethanol (10 mL) was added dropwise over a period of 15 min. The mixture was stirred at 65 C for 4 h. The mixture was cooled down to 0-5 C and NH4C1 (saturated aqueous solution, 20 mL) was added dropwise over a period of 10 min (foam.). Water (20 mL) was added and the yellow suspension was poured into dichloromethane (100 mL) and extracted with dichloromethane (4 x 75 mL). The combined organic layer was dried over MgS04 and concentrated in vacuo to give the product as light yellow solid (720 mg, 4.76 mmol, 91 %) which was used without further purification for the next step.MS: M = 150.1 (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,62135-58-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BACHMANN, Stephan; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RUDOLPH, Markus; WO2013/34506; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1074-98-2 ,Some common heterocyclic compound, 1074-98-2, molecular formula is C6H6N2O3, 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.

3-Methyl-4-nitropyridine 1-oxide (5.85 g) was dissolved in glacial acetic acid (115 mL) and hydrogenated in a Parr hydrogenation apparatus (catalyst: 220 mg Pt02 x 2 H20, 50 psi) at ambient temperature for 2.5 h. Then the catalyst was filtered off and the solvent was evaporated. After addition of 150 mL of water the pH was adjusted to 12 by addition of 2N NaOH. The resulting solution was extracted 10 times with 100 mL of dichloromethane (containing 5 % methanol). The combined organic phases were dried over anhydrous sodium sulphate and evaporated to give 3.81 g (83.6%) of 4-amino-3-methylpyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1074-98-2, its application will become more common.

Reference:
Patent; K.U. LEUVEN RESEARCH & DEVELOPMENT; GILEAD SCIENCES, INC.; PUERSTINGER, Gerhard; WO2005/63744; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem