Day: March 10, 2021

Synthetic Route of 579475-29-9, 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. 579475-29-9, name is 5-Bromo-2-cyclopropylpyridine, molecular formula is C8H8BrN, 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.

(0.21 g, 1.1 mmol), bis(pinacolato)diboron (0.31 g, 1.2 mmol) and potassium acetate (0.32 g, 3.2 mmol) were suspended in dioxane (10 mL). The slurry was degassed with argon for 10 minutes and then PdCl2X dppf (0.026 g) was added. The reaction mixture was heated to 80 C for 15 h and then, after cooling to RT, filtered through a Celite plug. The filtrate was concentrated to give a black oil that was dissolved in ether and extracted four times with 1.0M sodium hydroxide. The combined yellow water phases were cooled to 10 C, acidified with 2.5M hydrochloric acid to pH 6.5 and then extracted repeatedly with ether. The combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated to give 0.27 g (103%) of the title product as a yellow oil that slowly solidified. 1H-NMR suggested a purity of about 60-65% of the required product, the major contaminant being pinacolborane. The crude material was used without further purification.GC-MS mlz 245.2 (M+), 244.2 (M-I);1H-NMR(CDCl3) delta 8.78 (br s, IH), 7.93 (dd, IH), 7.10 (d, IH)5 2.10 (m, IH), 1.34 (s, 12H)5 1.10-1.00 (m, 4H) ppm.

According to the analysis of related databases, 579475-29-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2006/65215; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128071-98-7, 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. 128071-98-7, name is 4-Bromo-2-fluoropyridine. A new synthetic method of this compound is introduced below.

To a solution of LDA (2.0 M solution in THF) (12.79 mL, 25.6 mmol) in THF (20 mL) was added a solution of 4-bromo-2-fluoropyridine (3.0 g, 17.05 mmol) in THF (5 mL) dropwise at -78 C. The reaction mixture was stirred at-78 C for 1 h, then methyl iodide (1.599 mL, 25.6 mmol) was added. The reaction mixture was stirred at -78 C for 30 min, then stirred at rt for 0.2 h. The reaction mixture was diluted with water and the resulting mixture was extracted with ethyl acetate. The organic layer was separated and washed with brine, dried over MgSCk The filtrate was concentrated in vacuo. (0531) The residue was dissolved in DCM, purified via silica gel flash column chromatography, eluting with 0-15% ethyl acetate in hexane to give Intermediate 27A (colorless oil, 2.3 g, 12.1 mmol, 71% yield). LC-MS Anal. Calc’d for CeHsBrFN 188.96, found [M+H] 190, 192.1. Tr = 0.83 min (Method A). NMR (400MHz, DMSO-de) delta 7.97 (d, J=5.4 Hz, 1H), 7.63 (d, J=5.4 Hz, 1H), 2.30 – 2.29 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,128071-98-7, 4-Bromo-2-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-60-9, 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 131747-60-9, name is (2-Fluoropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Reference Production Example 5; A mixture of 0.64 g of 2-fluoro-4-pyridinemethanol, 10 ml of chloroform and 2.54 g of Dess-Martin Periodinane (1,1, 1-triacetoxy-l, 1-dihydro-l, 2- benziodoxol-3 (IH) -one) was stirred for 30 minutes at room temperature. A saturated sodium hydrogen carbonate aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.19 g of 2-fluoropyridine-4-carbaldehyde .1H-NMR (CDCl3) delta: 10.09 (d, J=I.2Hz, IH), 8.49 (d, J=4.9Hz, IH), 7.65-7.62 (m, IH), 7.38-7.36 (m, IH)

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 131747-60-9, (2-Fluoropyridin-4-yl)methanol.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKAHASHI, Masaki; IWAKOSHI, Mitsuhiko; IKEGAMI, Hiroshi; WO2010/125985; (2010); 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. 199296-40-7, name is tert-Butyl (5-formylpyridin-2-yl)carbamate, molecular formula is C11H14N2O3, 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. Product Details of 199296-40-7

100 g crude acrylic acid ester isomeric mixture prepared according to Example 3 was dissolved in 1 L HCl (5 N) and heated to reflux until complete conversion was achieved. The mixture was cooled to ambient temperature and the pH was adjusted to 7 with concentrated NaOH. The precipitate was filtered off and crystallized from boiling water to yield 25.2 g of 29 (E)-3-(6-Amino-pyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)-acrylic acid. [0288] 1H-NMR (600.2 MHz, CD4OD):=1.34 (m, 2H), 1.52 (m, 2H), 1.77 (m, 4H), 1.94 (m, 2H), 2.18 (m, 2H), 4.22 (dddd, J=1.52, 1.77, 7.42, 8.44, 1H), 6.51 (d, J=7.86 Hz, 1H), 7.19 (d, J=7.82 Hz, 1H), 7.41 (dd, J=4.22, 8.44 Hz, 1H), 7.82 (dd, J=7.19, 7.86 Hz, 1H), 7.86 (dd, J=7.19, 7.82 Hz, 1H), 8.44 (dd, J=4.22, 7.42 Hz, 1H). [0289] HPLC: tR=3.60 (Z) and 3.95 (E) min (YMC_C18 150¡Á4.6 mm, 3 mum, A: 9H2O+1 ACN/0.1 TEA/pH6.5 AcetAc, B: 1H2O+9 ACN/0.1 TEA/pH6.5 AcetAc, 0.8 mL/min, 20 C.

With the rapid development of chemical substances, we look forward to future research findings about 199296-40-7.

Reference:
Patent; SANOFI; BOEHM, Claudius; KLEIN, Susanne; NAPIERSKI, Bernard; SOMMER, Christian; US2013/245274; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86129-63-7, Adding some certain compound to certain chemical reactions, such as: 86129-63-7, name is Ethyl 2,4-dichloro-6-methyl-3-pyridinecarboxylate,molecular formula is C9H9Cl2NO2, 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 86129-63-7.

To a solution of 2- (IH-PYRAZOL-3-YL)-1, 3-THIAZOLE (7.71 g, 1.05 eq) in anh. DMF (61 mL), at 0C, under N2, was added NaH 60% in mineral oil (2.03 g, 1. 05 eq) and the reaction mixture was stirred for 10 min. at 0C and then for 1 hr at room temperature. Intermediate 1 (11.34 g, 48.0 MMOL) was then added as a solution in anh. DMF (35 mL) at 0C and the resulting solution was heated at 110C for 3 hr. The reaction was then quenched with water, extracted with EtOAc, washed with brine, dried over anh. NA2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7: 3) to give 7.02 g of the title compound as a white solid. NMR (‘H, CDCl3) : 8 7.91 (d, 1H), 7.91 (d, 1H), 7.41 (d, 1H), 7.31 (s, 1H), 7.18 (d, 1H), 4.50 (q, 2H), 2.78 (s, 3H), 1.25 (t, 3H). MS (M/Z) : 349 [MH] +.

According to the analysis of related databases, 86129-63-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); 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.97483-77-7, name is 5-Bromopicolinonitrile, molecular formula is C6H3BrN2, molecular weight is 183.01, as common compound, the synthetic route is as follows.Quality Control of 5-Bromopicolinonitrile

A solution of 5-bromo-2-pyridinecarbonitrile (2.0 g, 10.9 mmol) in dichloromethane (75 mL) was cooled to -78 degrees C., then a solution of DIBAL in toluene (1.5 M, 7.3 mL, 10.9 mmol) was added dropwise, taking care to keep the temperature below -65 degrees C. The resulting orange solution was stirred at -78 degrees C. for 5 h, then was allowed to gradually warm to 0 degrees C. The reaction was cooled back to -78 degrees C., then was quenched by dropwise addition of 20% aq. HCl. After warming to room temperature, the organic layer was separated, concentrated in vacuo and purified by chromatography to provide the product. The aqueous layer was treated with solid sodium bicarbonate until neutral, then this emulsion was extracted with ethyl acetate (3¡Á). These extracts were dried over sodium sulfate and concentrated in vacuo to provide additional product, 5-bromo-2-pyridinecarbaldehyde. 1H NMR (400 MHz, CDCl3) delta 7.85 (d, J=8.18 Hz, 1H), 8.02 (d, J=8.18 Hz, 1H), 8.85 (s, 1H), 10.03 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,97483-77-7, 5-Bromopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60290-21-3, 4-Chloro-1H-pyrrolo[3,2-c]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, 60290-21-3, blongs to pyridine-derivatives compound. Recommanded Product: 4-Chloro-1H-pyrrolo[3,2-c]pyridine

Cul (110 mg, 0.12 mmol), /rans-N, N?-dimethylcyclo hexane- 1, 2-diamine (37.9 iiL, 0.24 mmol) and K2C03 (332 mg, 2.40 mmol) were added to a stirred solution of 4- chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (238 mg, 1.56 mmol) and 4-iodo-l- methyl-lH-imidazole [71759-87-0] (250 mg, 1.20 mmol) in toluene (5 mL). The reaction mixture was stirred at 105 C for 24 h, cooled to room temperature and partitioned between NaHCCL (sat., aq.) and EtOAc. The aqueous phase was extracted with EtOAc (twice). The combined organic phases were washed with brine, dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 0:100) to afford 1-139 (120 mg, 43%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60290-21-3, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102368-13-8, 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. 102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one). A new synthetic method of this compound is introduced below.

Step D: 4-Isothiocyanato-6-(methoxymethyl)pyrimidine To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.84 g, 3.59 mmol) was in dichloromethane at ambient temperature was added 6-(methoxymethyl)pyrimidin-4-amine (0.5 g, 3.59 mmol). The orange solution was stirred at ambient temperature for 18 h. The solution was purified by column chromatography (0-40% ethyl acetate/hexanes) to afford 4-isothiocyanato-6-(methoxymethyl)pyrimidine (0.32 g, 1.77 mmol, 49% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.91 (1H, d, J=1.26 Hz), 7.19 (1H, d, J=1.01 Hz), 4.52 (2H, s), 3.49 (3H, s). MS (LC/MS) R.T.=1.39; [M+H]+=182.10.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102368-13-8, 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1945-84-2, 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. 1945-84-2, name is 2-Ethynylpyridine. A new synthetic method of this compound is introduced below.

General procedure: To a stirred solution of alkyne (1 mmol) in CH2Cl2 (3 mL), TsNBr2 (1.2 mmol) and DBU (1.2 mmol) was added. The progress of the reaction was monitored by TLC. After the completion of the reaction sodium thiosulfate (200 mg) was added to the reaction mixture and further stirred for 5 min. The reaction mixture was washed with water and extracted with ethyl acetate. The organic layer was separated and dried over Na2SO4 and concentrated in vacuo. Purification of the crude product by flash chromatography on silica gel (230-400mesh) with petroleum ether as eluent gave the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1945-84-2, 2-Ethynylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Rajbongshi, Kamal Krishna; Hazarika, Debojit; Phukan, Prodeep; Tetrahedron; vol. 72; 29; (2016); p. 4151 – 4158;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-82-3 ,Some common heterocyclic compound, 153034-82-3, molecular formula is C6H3FINO, 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 dry 15mL ChemGlass pressure bottle under N2 was added 4-iodo-2- fluoro-3-formylpyridine (314 mg, 1.25 mmol), (2-chloro-4-fluorophenyl)hydrazine (210 mg, 1.31 mmol), and anhydrous NMP (5 mL). The reaction mixture was purged with argon, heated at 185C for 2h, and then at 140C for 36h. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the crude product was purified by Biotage Silica gel chromatography using a 80g Thompson Single Step silica cartridge with a linear gradient from 100% hexanes to 100% CH2CI2 over 12 column volumes to give 63.5 mg (13.6%) of the title compound as a pale yellow solid, LC/MS (Condition B): ret. T = 3.7 min, (M+H)+ 373.88, 375.88 and 149.3mg (30.3%) of the hydrazone intermediate as a pale yellow solid, LC/MS (Condition B): ret. T = 4.2min, (M+H)+ 393.90, 395.90.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-82-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem