Day: June 22, 2021

Synthetic Route of 76006-08-1, 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. 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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.

5-bromo-2-methyl-2H-indazole (515 mg, 2.44 mmol) and (0404) bis[(tetrabutylammonium iodide)copper(I) iodide] (456 mg, 0.407 mmol) were combined in a reaction vessel, followed by5-chloro-lH-pyrazolo[3,4-c]pyridine (250 mg, 1.628 mmol), trans- N,N’-dimethylcyclohexane-l,2-diamine (0.257 ml, 1.628 mmol), and anhydrous K3P04 (691 mg, 3.26 mmol). This mixture was then evacuated and backfilled with N2 (3 times). Anhydrous degassed dioxane (20 ml) was added to this flask. This mixture was again evacuated and backfilled with N2 (3 times) and then as heated at 110C for 22h. LCMS showed a peak consistent with product. The reaction was diluted with EtOAc and water. The blue colored aqueous layer was separated from the green colored organic layer. The aqueous layer was extracted with EtOAc. The combined organics were filtered and concentrated. The residue was purified by column chromatography on silica gel (24g), eluting with 1-100 % EtOAc/hexanes to give 5-chloro-l-(2-methyl-2H-indazol-5-yl)-lH-pyrazolo[3,4-c]pyridine LCMS: M+H = 284

According to the analysis of related databases, 76006-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19524-06-2, 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. 19524-06-2, name is 4-Bromopyridine hydrochloride. A new synthetic method of this compound is introduced below.

Zinc bromide (502 g, 2.23 mole) was added in approximately 100 g portions to 2.0 L of tetrahydrofuran cooled to between 0 and 10°C. To this cooled solution was added 4- bromopyridine hydrochloride (200 g, 1.02 mol), triphenylphosphine (54 g, 0.206 mol), and palladium (II) chloride (9.00 g, 0.0508 mol). Triethylamine (813 g, 8.03 mol) was then added at a rate to maintain the reaction temperature at less than 10°C, and finally trimethylsilylacetylene (202 g, 2.05 mol) was added. The mixture was heated to 60°C for 4.5 hours. The reaction was cooled to -5°C and combined with 2.0 L of hexanes and treated with 2 L of 7.4 M NH4OH. Some solids were formed and were removed as much as possible with the aqueous phase. The organic phase was again washed with 2.0 L of 7.4 M NH4OH, followed by 2 washes with 500 mL of water, neutralized with 1.7 L of 3 M hydrochloric acid, dried with sodium sulfate, and concentrate to a thick slurry. The slurry was combined with 1.0 L of hexanes to give a precipitate. The precipitate was removed by filtration and the filtrate was concentrated to 209 g of dark oil. The product was purified by distillation (0.2 torr, 68°C) to give 172 g (96percent) of Compound (VI) as colorless oil. Analytical data: NMR (500 MHz, DMDO-de) delta 8.57 (2 H), 7.40 (2 H), 0.23 (9 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19524-06-2, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; KOPACH, Michael, E.; WILSON, Thomas, Michael; KOBIERSKI, Michael, Edward; (35 pag.)WO2017/31215; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, 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.

l-(6-fluoropyridin-3-yl)prop-2-yn-l-yl acetate : 6-fluoronicotinaldehyde (300 mg, 2.40 mmol) was dissolved in THF (15 mL) and brought to 0 C. Ethynylmagnesium bromide (0.5 M in THF, 5.76 mL, 2.88 mmol) was added slowly and the resulting solution allowed to stir for 30 minutes. Acetic anhydride (0.45 mL, 4.80 mmol) was then added, the cold bath removed, and the reaction mixture allowed to warm to room temperature over 2 hours. The reaction contents were quenched by the addition of saturated aqueous NH4C1 (5 mL), poured into water (5 mL), and extract with EtOAc (3 x 15 mL). The combined organic phase was washed with brine (10 mL), dried over MgS04 and concentrated. The crude residue was purified by flash chromatography (eluent: EtOAc / hexanes) to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-Hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (604 pag.)WO2017/7689; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1594-58-7, Adding some certain compound to certain chemical reactions, such as: 1594-58-7, name is N-Hydroxynicotinimidamide,molecular formula is C6H7N3O, 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 1594-58-7.

General procedure: The newly synthesized acyl chloride dissolved intoluene (10 mL) was slowly added to a solution ofamidoxime (2.5 mmol) dissolved in toluene (40 mL) in a250 mL round-bottomed flask at 25 oC and under constantstirring. After the addition, the solution was refluxed for20 h, and then washed with sodium carbonate solution. Theorganic phase was dried with anhydrous sodium sulfateand thereafter the toluene was removed under vacuumby heating. A solid was obtained, which was purified byfash column chromatography using a hexane/ethyl acetatemixture as eluent with an increasing polarity gradient (9:1to 6:4).20

According to the analysis of related databases, 1594-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cunha, Felipe S.; Nogueira, Joseli M. R.; De Aguiar, Alcino P.; Journal of the Brazilian Chemical Society; vol. 29; 11; (2018); p. 2405 – 2416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211534-25-6, 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. 1211534-25-6, name is 4-Bromo-5-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, 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.

[00257j 27F. 4-((3 ,4-cis)-4-((tert-Butyldimethylsilyl)oxy)-3 -methylpiperidin- l-yl)-5 – chloro-2-methoxypyridine: A mixture of 27B (9.70 g, 43.6 mmol), 27E (10.0 g, 43.6mmol), and K2C03 (12.0 g, 87.0 mmol) in DMSO (14.5 mL) was vigorously stirred at110 C overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and concentrated. Purification via silica chromatography gave 27F as an oil (14.3 g, 77% yield). LC-MS Anal. Calc?d for C18H31C1N2O2Si: 370.18, found [M+H] 371.2.

According to the analysis of related databases, 1211534-25-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ELLSWORTH, Bruce, A.; JURICA, Elizabeth, A.; SHI, Jun; EWING, William, R.; YE, Xiang-Yang; WU, Ximao; ZHU, Yeheng; SUN, Chongqing; WO2014/78609; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-98-0, 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 13534-98-0, name is 4-Amino-3-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Ethyl (3-bromopyridin-4-yl)carbamate (S7).3-Bromopyridin-4-amine (100 mol%) was dissolved in CH2Cl2 (0.2 M), and cooled to 0 C. Ethyl chloroformate (110 mol%) was added at 0 C, then diisopropylethylamine (150 mol%) was added. The mixture was stirred at 0 C for 30 min, warmed to ambient temperature, and stirredor additional 2-3 h. After completion, the mixture was diluted with CH2Cl2, and washed withwater and brine. The combined aqueous layer was washed with CH2Cl2. The combined organiclayer was dried over anhydrous Na2SO4, and concentrated in vacuo. The title compound S7 was obtained as an off white solid in 86% yield (610.6 mg, 2.49 mmol) after flash column chromatography (hexanes/EtOAc = 1:1). 1H NMR (asterisk denotes minor rotamer peaks, 400 MHz, CDCl3) delta 8.82* (d, J = 0.5 Hz, 1H), 8.59* (d, J = 5.6 Hz, 1H), 8.59 (d, J = 0.4 Hz, 1H), 8.40 (dd, J = 5.6, 0.6 Hz, 1H), 8.15 (d, J =5.6 Hz, 1H), 7.30 (br s, 1H), 7.22* (dd, J = 5.1, 0.5 Hz, 1H), 4.28 (q, J = 7.1 Hz, 2H), 4.24* (q, J= 7.1 Hz, 2H), 1.35 (t, J = 7.1 Hz, 3H), 1.23* (t, J = 7.1 Hz, 3H). 13C NMR (asterisk denotes minor rotamer peaks, 100 MHz, CDCl3) delta 153.0*, 152.4*, 151.6,149.5, 142.8, 124.7*, 113.2, 109.7, 63.8*, 62.2, 14.4, 14.0*. IR (neat) 3405, 2980, 1739, 1582, 1506, 1236, 1205 cm-1.HRMS (ESI+) calcd. for C8H10BrN2O2 [M+H]+ 244.9920, found 244.9920.

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 13534-98-0, 4-Amino-3-bromopyridine.

Reference:
Article; Shin, Inji; Ramgren, Stephen D.; Krische, Michael J.; Tetrahedron; vol. 71; 35; (2015); p. 5776 – 5780;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113975-22-7, 2-Fluoro-3-iodopyridine, 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, HPLC of Formula: C5H3FIN, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3FIN

General procedure: 1-(Indol-3-yl)-N-Boc-THIQ 4a (100 mg, 0.287 mmol, 1.0 equiv.), iron(III)-chloride (4.7 mg, 28.7 mumol, 0.1 equiv.), and K3PO4 (122 mg, 0.574 mmol, 2.0 equiv.) were placed in a 2 mL glass vial, and aryliodide (0.431 mmol, 1.5 equiv.) and DMEDA (5.6 muL, 57.4 mumol, 0.20 equiv.) were added followed by dry toluene (300 muL). The reaction mixture was purged with argon for 30 seconds, the vial sealed and heated to 135 C and stirred at this temperature for 24 hours. The black slurry was cooled down to rt, diluted with DCM and filtered through a plug of celite. The solvent of the filtrate was evaporated and the crude product directly subjected to column chromatography using gradient elution with PE_EtOAc=100:0 0:40 (50 minutes) to afford the desired products 7a-e,g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113975-22-7, 2-Fluoro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Article; Ghobrial, Michael; Mihovilovic, Marko D.; Schnuerch, Michael; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2186 – 2199;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18614-51-2, 4-Amino-2-fluoropyridine, 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, 18614-51-2, blongs to pyridine-derivatives compound. Recommanded Product: 18614-51-2

Method A) CuCl2 (0.0680 g, 0.513 mmol) was dissolved in 3 mL of water to yield a blue,opaque solution. 2-F-4-AP (0.111 g, 0.991 mmol) in 5 mL of water was added to the CuCl2solution. The aquamarine, opaque solution was left to evaporate at room temperature forthree weeks. Dark green prisms were recovered by vacuum filtration, washed with cold waterand allowed to air dry to give 0.0612 g (13.7%). Single crystals (dark green needles) weregrown through recrystallization of the prisms from water over the course of a month. IR (KBr)nu – 3413 m, 3327 m, 3220 m, 3071w, 1639s, 1560 m, 1510 m, 1475 m, 1375s, 1267s, 1195 m,1026 m, 994 m, 834 m, 777 m, and 656w cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18614-51-2, its application will become more common.

Reference:
Article; Krasinski, Claire A.; Solomon, Benjamin L.; Awwadi, Firas F.; Landee, Christopher P.; Turnbull, Mark M.; Wikaira, Jan L.; Journal of Coordination Chemistry; vol. 70; 5; (2017); p. 914 – 935;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 63071-03-4, 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 63071-03-4 as follows.

BuLi (2.5 M, 49.0 ml, 122 mmol) was added to a solution of 2-methoxy-6-methylpyridine in THF (300 ml) at -78 C. over a period of 30 min. After warming the mixture to 0 C. over a period of 1 h, the reaction was re-cooled to -78 C. and acetaldehyde (22.3 ml, 407 mmol) was slowly added. The mixture was stirred for 1 h at -78 C. and allowed to warm to ambient temperature. Addition of sat. aq. NH4Cl and extraction with EtOAc was followed by a wash of the organic layer with sat. aq. NaHCO3 and brine. Concentration of the organic layer in vacuo and chromatographic purification of the resulting residue gave 8.96 g (66%) of 1-(6-methoxypyridin-2-yl)propan-2-ol. 1H-NMR (CDCl3) delta 7.51 (dd, 1H), 6.71 (d, 1H), 6.63 (d, 1H), 5.18 (br s, 1H), 4.21 (qdd, 1H), 3.91 (s, 3H), 2.84 (dd, 1H), 2.77 (dd, 1H), 1.28 (d, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63071-03-4, its application will become more common.

Reference:
Patent; Forest Laboratories Holdings Limited; US2007/281918; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 845827-14-7, 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. 845827-14-7, name is 2-Bromo-5-(difluoromethoxy)pyridine. A new synthetic method of this compound is introduced below.

Production Example 23 4-[5-(Difluoromethoxy)-2-pyridyl]benzenecarboxylic acid Operations similar to those of Production Example 14 were conducted using 4-carboxyphenylboronic acid and 2-bromo-5-(difluoromethoxy)pyridine, to provide the title compound as white solid. ESI-MS Found:m/z 266[M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,845827-14-7, 2-Bromo-5-(difluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1657242; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem