Day: April 14, 2022

Application of 89282-03-1 ,Some common heterocyclic compound, 89282-03-1, molecular formula is C5H4INO, 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.

Dry DMF (6.0 mL) was added to methyl 4-hydroxy-3-iodobenzoate (0.56 g, 2.0 mmol), ethynylboronic acid MIDA ester (0.47 g, 2.6 mmol), CuI (38 mg, 0.20mmol), PdCl2(Ph3P)2 (70 mg, 0.10 mmol) and Ph3P (52 mg, 0.20 mmol) under N2. 1,1,3,3-Tetramethylguanidine(TMG) (0.30 mL, 2.4 mmol) was added to the resulting solution under N2. The reactionmixture was stirred at 50 Cfor 22 h under N2. The resulting mixture was diluted with water to form aprecipitate, which was filtered, washed with water and dried at room temperature. The obtained solid was dissolved in acetone and purified by flash chromatography (SiO2, CH2Cl2 : MeOH = 10 : 1). The eluted material was washed with hot EtOH and dried to give 1A (493.6 mg, 75%) as a pale brown solid; Furo[3,2-c]-2-boronic acid (13): Prepared from 4-hydroxy-3-iodopyridine and ethynylboronic acidMIDA ester. The resulting mixture was diluted with water and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2,CH2Cl2 : MeOH = 10 : 1) to give 180.7 mg of 1 : 1 mixture of MIDA boronate and boronic acid as a pale yellow powder (41%). The mixture was treated with hot EtOH to afford 13 (109.9 mg, 34%) as a paleyellow solid; IR (cm-1) 3000, 1736, 1616, 1591, 1570, 1541, 1473, 1373, 1356, 1300, 1228, 1164, 1145,1039; 1H-NMR (DMSO-d6) delta 7.57 (d, J = 0.5 Hz, 1H), 7.65 (d, J = 6.0 Hz, 1H), 8.46 (d, J = 6.0 Hz, 1H),9.00 (s, 1H); HRMS calcd for C7H7NO3B [M+H] 164.0514, found 164.0513 (Delta 0.05).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.

Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
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. 89402-42-6, name is 2,3-Difluoro-5-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., Product Details of 89402-42-6

Example 4 3-Fluoro-2-phenylthio-5-trifluoromethylpyridine At 148-156 C., 59.6 g (0.326 mol) of 2,3-difluoro-5-trifluoromethylpyridine were added over a period of 2.5 h to 37.7 g (0.338 mol) of 98.7% pure thiophenol and 2.1 mg (0.01 mol %) of copper powder, and the mixture was stirred at 156-164 C. for 2 hours. After cooling, the residue was taken up in methylene chloride, washed with 0.5 N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure. 88.9 g (100% of theory) of the title compound of

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, 89402-42-6, 2,3-Difluoro-5-(trifluoromethyl)pyridine.

Reference:
Patent; BASF Aktiengesellschaft; US6191280; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17282-01-8, 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 17282-01-8, name is 3-Bromo-2-fluoro-5-picoline. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-bromo-2-fluoro-5-methylpyridine (202 mg, 1.06 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (300 mg, 1.17 mmol), potassiumacetate (208 mg, 2.12 mmol) and PdCh(PPh3h (37 mg, 0.053 mmol) in dioxane (4 mL) wasstirred for 3 hours at 100C. To the mixture was added di-tert-butyl(6′-bromotrispiro[cyclobutane-1,2′-chromene-4′,4″-[1,3]oxazole-3′,3″‘-oxetan]-2″-yl)imidodicarbonate (300 mg, 0.531 mmol), sodium carbonate (225 mg, 2.12 mmol) and H20 (1 mL),and the mixture was stirred for 1.5 hours at 100 oc. The mixture was treated with charcoal,and filtered off. The filtrate was partitioned between EtOAc and water. The organic layer waswashed with brine, dried over MgS04 , filtered, and the filtrate was evaporated to give a palebrown oil. The oil was dissolved in toluene (5 mL) and to the mixture was added silicagel(neutral; 600 mg). The mixture was refluxed for 1 hour. The solvent was evaporated off. Silicagel column chromatography (CHCh-EtOH, linear gradient of EtOH from 0 to 20%)afforded a solid. The solid was triturated in Et20 and collected by filtration, washed with Et20and dried in vacuo at 70 octo give6′-(2-fluoro-5-methylpyridin-3-yl)trispiro[cyclobutane-1,2′-chromene-4′,4″-[1,3]oxazole-3’,3″‘-oxetan]-2″-amine (130 mg).

According to the analysis of related databases, 17282-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTELLAS PHARMA INC.; COMENTIS, INC.; MUNAKATA, Ryosuke; INOUE, Makoto; TOMINAGA, Hiroaki; YAMASAKI, Shingo; SHIINA, Yasuhiro; SAMIZU, Kiyohiro; HAMAGUCHI, Hisao; HONG, Lin; WO2013/181202; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10128-72-0, 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.10128-72-0, name is Methyl 3-hydroxyisonicotinate, molecular formula is C7H7NO3, molecular weight is 153.14, as common compound, the synthetic route is as follows.

[0166] To a solution of chloride (200 mg, 1.0 mmol, 1.0 eq), and phenol (153 mg, 1.0 mmol, 1.0 eq) in DMF (15 mL) was added K2C03 (414 mg, 3.0 nimol, 3.0 eq) and the reaction mixture was heated at 8 0-90 C for 5 h. Solvent was removed and the residue was purified by column chromatography (EtOAc/ MeOH) to give the alkylation product. MS: exact mass calculated for C15H13N303, 283.10; m/z found, 284 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 10128-72-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102145; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142197-14-5 ,Some common heterocyclic compound, 1142197-14-5, molecular formula is C8H8BrN, 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.

A mixture of tert-butyl 4-(5-amino-lH-pyrazol-3-yl)piperidine-l-carboxylate (300 mg, 1.126 ramol), 2-bromo-5-cyclopropylpyridine (234mg, 1.183mmol), copper(I) iodide (21.45mg, 0.1 13mmol), (lS,2S)-NN2-dime ylcyclohexane-l,2-diamine (16.02 mg, 0.113 mmol), and cesium carbonate (734mg, 2.253 mmol), DMSO (3 rnL), was purged with N2 for 30 min. The mixture was heated to 130 C in a sealed tube for 15 h. The mixture was cooled to rt. and water (30 mL) was added. The mixture was extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel chromatography, eiuting with a solvent gradient of 0 to 40 % EtOAc in hexanes to give the product as a white solid. 1H NMR (400 MHz, CDC13) delta 8.03 (m, 1H), 7.74 (m, 1H), 7.32 (m, 1H), 5.88 (bs, 2H), 5.26 (s, 1H), 4.10 (m, 2H), 2.79 (m, 2H), 2.67 (m, 1H), 1.88-1.79 (ra, 3H), 1.61-1.54 (m, 2H), 1.42 (s, 9H), 1.20(t, J- 7.2 Hz, 1H), 0.94 (m, 2H), 0.63 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1142197-14-5, 2-Bromo-5-cyclopropylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCELROY, William, T.; LI, Guoqing; HO, Ginny Dai; TAN, Zheng; PALIWAL, Sunil; SEGANISH, William Michael; TULSHIAN, Deen; LAMPE, John; METHOT, Joey, L.; ZHOU, Hua; ALTMAN, Michael, D.; ZHU, Liang; WO2012/129258; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 695-98-7, 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. 695-98-7, name is 2,3,5-Trimethylpyridine, molecular formula is C8H11N, 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 1 Bis(bis(trimethylsilyl)amido)bis(2,3,5-collidine)magnesium A 100-mL Schlenk flash was charged with bis(bis(trimethylsilyl)amido)bis(tetrahydrofuran)-magnesium (0.200 g, 0.460 mmol), a magnetic stir bar, and benzene (40 mL). 2,3,5-collidine (0.12 g, 0.91 mmol) was then added to this solution. The mixture was stirred for 18 h at room temperature. The volatile components were removed at reduced pressure to afford a yellow-orange solid. This solid was extracted into hexane (10 mL) and the resultant solution was filtered through a 2-cm pad of Celite.(R).. The filtrate was cooled to -20° C. for 18 h to afford colorless blocks of 1 (0.18 g, 66percent). Spectroscopic and analytical data for 1: mp 72°-73° C.; IR (Nujol, cm-1) 1249 (s), 1211 (m), 1148 (m), 1021 (s), 973 (s), 887 (s), 841 (s), 782 (s), 738 (s), 725 (s), 661 (s), 610 (s), 537 (s); 1 H NMR (C6 D6, delta) 8.39 (s, 2,3,5-collidine C-H), 6.63 (s, 2,3,5-collidine C-H), 2.43 (s, 2,3,5-collidine CH3), 1.81 (s, 2,3,5-collidine CH3), 1.69 (s, 2,3,5-collidine CH3), 0.33 (s, Si(CH3)3); 13 C{1 H} NMR (C6 D6, ppm) 154.32 (s, 2,3,5-collidine C-CH3), 147.00 (s, 2,3,5-collidine C-H), 139.41 (s, 2,3,5-collidine C-H), 132.00 (s, 2,3,5-collidine C-CH3), 131.26 (s, 2,3,5-collidine C-CH3), 22.04 (s, 2,3,5-collidine C-CH3), 18.62 (s, 2,3,5-collidine C-CH3), 17.45 (s, 2,3,5-collidine C-CH3), 5.87 (s, Si (CH3)3); Anal. Calcd for C28 H58 MgN4 Si4: C, 57.25; H, 9.95; N, 9.54. Found: C, 56.25; H, 10.00; N, 9.61.

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 695-98-7, 2,3,5-Trimethylpyridine.

Reference:
Patent; Wayne State University; US5892083; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 946002-90-0, 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.946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, molecular formula is C9H11BrN2O, molecular weight is 243.1, as common compound, the synthetic route is as follows.

(R)-5-Bromo-2-[3-(2,6-dichloro-4-methyl-phenoxy)-pyrrolidin-l-yl]-pyridine. ADDP (11.7 g, 45.4 mmol) was added to a sol. of compound Gl (8.82 g, 36.3 mmol) and 2,6-dichloro-/?-cresol (7.37 g, 40.0 mmol) in toluene (200 mL). The mixture was degassed with nitrogen for 5 min, and PBu3 (85%, 15.8 mL, 46.2 mmol) was added. The mixture was heated rapidly to 100 0C, and stirred at this temperature for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane (200 mL). The mixture was filtered, and the filtrate was evaporated under reduced pressure. Purification of the residue by FC (EtO Ac/heptane 1 :7) yielded a crude title compound that was diluted with CH2Cl2. This mixture was washed with aq. IM NaOH. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the pure title compound (13.5 g, 93%). LC-MS: tR = 0.92 min; ES+: 402.98.

The chemical industry reduces the impact on the environment during synthesis 946002-90-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
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. 896722-51-3, name is 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C14H12N2O2S

A solution of 50% NaOH (0.573 g) was added to N-protected 6-methyl-7-azaindole (0.390 g, 1.43 mmol) in Ethanol (10 mL). After refluxed for 8 h, the mixture was concentrated and was extracted with CHCl3. The organic layer was washed with water and dried. The solvent was evaporated in vacuo and the residue was purified on a silica gel column eluting with EtOAc/hexane (1:3) to give 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.148 g, 78%).

The synthetic route of 896722-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used ?as is? in the step of Example 3 below. ; Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, 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, Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (1.19 g, 5.87 mmol), triethylamine (2.97 g, 29.3 mmol), and crude trifluoroacetic acid salt of piperidine-4- carboxylic acid isobutyl amide [obtained by stirring 4-isobutylcarbamoyl-piperidine-1- carboxylic acid te/f-butyl ester (2.63 g, 8.80 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (6 mL) for 1.5 hours, then removing solvents by rotary evaporation] in dioxane (10 mL) is heated in a 75 mL sealed tube at 120 0C for 68 h. Filtration of room temperature mixture does not lead to separation of regioisomers. The filtrate is concentrated down to dryness by rotary evaporation, dissolved into ethyl acetate, and then washed with water and brine. The organic layer is dried over sodium sulfate, filtered and concentrated down to dryness by rotary evaporation. This residue is then combined with solids from first filtration and eluted through a silica gel column (80:20 ethyl acetate / heptane, then 100% ethyl acetate, then 95:5 ethyl acetate / methanol). The more polar regioisomer (TLC solvents: 90:10 ethyl acetate / methanol) is concentrated down to dryness by rotary evaporation, then treated with a small amount of methanol. The pink solid is isolated by filtration (0.647 g, 1.84 mmol, 31 %). MS(ESI) m/z 351.20 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.00 (s, 1 H), 7.79 (t, J=5.81 Hz, 1 H), 6.84 (s, 1 H), 4.54 (s, 2 H), 4.19 (d, J=13.39 Hz, 2 H), 3.09 – 2.92 (m, 2 H), 2.86 (dd, J=6.57, 6.06 Hz, 2 H), 2.48 – 2.36 (m, 1 H), 1.79 – 1.71 (m, 2 H), 1.71 – 1.52 (m, 3 H), 0.82 (d, J=6.82 Hz, 6 H).

The synthetic route of 1201676-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem