Day: March 1, 2022

Application of 936841-69-9, 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 936841-69-9 as follows.

To a solution of 4-(trifluoromethyl)pyridine-2-carbonitrile (1.7 g, 9.88 mmol) in methanol (18 ml) was added sodium methoxide (25 wt% in MeOH) (2.1 g, 9.9 mmol, 2.3 ml) and the mixture stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness, the residue suspended in methylamine (33 wt% in EtOH) (25 ml, 200.9 mmol) to which was added methylamine hydrochloride (6.7 g, 99.2 mmol). The reaction mixture was heated in a closed high pressure vial at 90C overnight. After cooling, the mixture was concentrated and the residue treated with dichloromethane, filtered and the filtrate evaporated under reduced pressure. This material was dissolved in diethyl ether, treated with a 2M hydrochloric acid solution in diethyl ether under cooling, stirred at 5-10C for 20 minutes, then diluted with water. The layers were separated and the organic phase washed twice with water. The combined aqueous phases were basified to pH 12 by addition of an aqueous 30% sodium hydroxide solution under cooling, and the product thoroughly extracted with diethyl ether (4x). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford N,N’-dimethyl-4-(trifluoromethyl)pyridine-2-carboxamidine as an oil (0.70 g), which was used without further purification. LCMS (method 1 ): 218 (M+H)+, retention time 0.28 min. 9F-NMR (MeOD, ppm) -66.4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936841-69-9, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; EMERY, Daniel; BUCHHOLZ, Anke; (145 pag.)WO2017/16910; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 167884-17-5, 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. 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol. A new synthetic method of this compound is introduced below.

To a solution of imidazo[l,2-a]pyridin-5-ylmethanol (0.150 g, 1.01 mmol, 1 eq) in DMF (2 mL) was added ethyl 3-bromopropanoate (367 mg, 2.02 mmol, 2 eq), NaOH (121 mg, 3.04 mmol, 3 eq) and TBAI (3.74 mg, 0.010 mmol, 0.01 eq). The mixture was stirred for 16 h at 50C. The reaction was quenched with water (10 mL), the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgS04 and concentrated in vacuo. The residue was purified by prep-TLC (Si02, DCM/MeOH = 10/1, Rf = 0.42) to give ethyl 3-(imidazo[l,2-a]pyridin-5-ylmethoxy)propanoate (0.04 g, 13% yield, 80% purity) as a yellow oil, LCMS: m/z = 249.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; PIPELINE THERAPEUTICS, INC.; XIONG, Yifeng; SCHRADER, Thomas; CHEN, Austin; ROPPE, Jeffrey Roger; BACCEI, Jill Melissa; BRAVO, Yalda; (199 pag.)WO2019/241131; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84539-34-4 ,Some common heterocyclic compound, 84539-34-4, molecular formula is C5H4Br2N2, 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.

Example 77: 3-(benzenesuIfoiiyl)-7-bromo-1H-pyrrolo[3, 2-cjpyridin- 2-amine To a stirred and nitrogen degassed solution of 3,5-dibromopynchn-4-amine (CM 84539-34-4; 2.5 g, 9.92 mmol), tetrakis(triphenylphosphane) palladium (287 mg, 248 itmol) in anhydrous DME (20 mL) was added a solution of 2- (benzenesulfonyl)acetonitrile (CM 7605-25-9; 1.98 g, 10.92 nimol) and sodium hydride (992 mg, 24.81 mmol, 6o% dispersion in oil) in anhydrous DME (12 mL). The reaction mixture was heated under microwave irradiation at 130 C for 2 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organics were filtered and dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica, o-ioo% EtOAc / petroleum ether) to afford the title compound.?H NMR (400 MHz, DMSO-d6) 6 ppm 6.6 (br. s., 2 H) 7.40 – 7.64 (m, 3 H) 7.91 – 7.98 (m, 2 H) 8.i8 (s, 1 H) 8.54 (hr. s., 1 H) 11.57 (s, 1 H).MS ESi 354

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84539-34-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LTD; BARKER, Gregory; DAVENPORT, Richard; DOWNHAM, Robert; FARNABY, William; GOLDBY, Anne; HANNAH, Duncan; HARRISON, David; WILLEMS, Henriette; (390 pag.)WO2015/198045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1227594-89-9, Adding some certain compound to certain chemical reactions, such as: 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one,molecular formula is C6H3F4NO, 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 1227594-89-9.

[00778] Step C: A solution of triphenylphosphine (39 mg, 0.149 mmol) in THF (1 mL) at room temperature was treated with DIAD (29 muL, 0.149 mmol). The mixture was stirred for 10 min and then tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1r,4S)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (50.9 mg, 0.099 mmol) was added in THF (1 mL), followed by 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (36 mg, 0.199 mmol). The mixture stirred overnight and partitioned between water (15 mL) and EtOAc (10 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silca gel (20-70% EtOAc in hexanes) to afford tert-butyl (3-(1-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-1-((1s,4R)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (77.7 mg, 115% yield).

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. 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); 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. 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide. A new synthetic method of this compound is introduced below., Recommanded Product: 1026796-81-5

NaH (43 mg, 1.88 mmol) was added to a solution of N-(4-bromo-2- pyridyl)acetamide (337 mg, 1.57 mmol) in THF (3 mL) at 0 C. Iodomethane (98 m, 1.57 mmol) was added and the resulting mixture was stirred at rt overnight. EtOAc was added and the mixture was washed with water, dried over MgSCri. filtered, concentrated and purified on a silica gel column eluted with 0-100% EtOAc in heptane to give the product as a solid (208 mg, 58%). MS ES+ m z 229 [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, 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); 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. 113270-73-8, name is 2-(4-Bromophenyl)-1H-imidazo[4,5-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 113270-73-8

2-(4-Bromo-phenyl)-3H-imidazo[4,5-c]pyridine (Preparation 12A) (0.25 g, 0.912 mmol), 4-methoxyphenylborrhonic acid (0.20 g, 1.32 mmol), tetrakis(triphenylphosphine)palladium (0) and potassium carbonate (0.126 g, 2.32 mmol) in ethanol/water (13 mL/1.5 mL) were refluxed for 2.5h. The mixture was diluted with ethanol (20 mL) and water (20 mL), filtered (Celite) and concentrated. The residue was triturated with saturated aq. NaHCO3 (20 mL), water and ether (50 mL) to give 0.26 g (95%) of 2-(4′- methoxy-biphenyl-4-yl)-3H-imidazo[4,5-c]pyridine as a light pink-tan tietated solid which had: mp > 2600C; NMR (DMSO-d6) delta 8.90 (s, 1 H), 8.26 (d, J = 5.4 Hz, ,1 H), 8.22 (d, J = 8.7 Hz, 2H), 7.81 (d, J = 8.7 Hz, 2H), 7.70 (d, J = 9.1 Hz, 2H), 7.55 (d, J = 5.4 Hz, 1 H), 7.02 (J = 8.7 Hz, 2H), 3.77 (S, 3H).

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, 113270-73-8, 2-(4-Bromophenyl)-1H-imidazo[4,5-c]pyridine.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/34277; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 78473-10-6, 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.78473-10-6, name is 2-Aminopyridine-3,5-dicarbonitrile, molecular formula is C7H4N4, molecular weight is 144.1335, as common compound, the synthetic route is as follows.

Step B 2-Chloro-3,5-dicyanopyridine Acetic acid (37 mL) was added over 10 min to sodium nitrite (13.4 g, 0.194 mol) with stirring. Concentrated sulfuric acid (12.3 mL) was added over 5 min to the resulting thick slurry which was then cooled to 0 C. In a separate flask, pyridinium hydrochloride (14.4 g, 0.125 mol) was added to a stirred mixture of 2-amino-3,5-dicyanopyridine (4.0 g, 27.75 mmol) in acetic acid (55 mL) and the resulting mixture was cooled to 0 C. to give a thick slurry. The nitrite slurry was added to the aminopyridine slurry over 5 min with stirring at 0 C. Acetic acid (50 mL) was added and the thick slurry was warmed to rt. After 1 h at rt the mixture was warmed to 50 C. and after a further 1 h, it was poured into an ice/water mixture (500 mL). The aqueous mixture was extracted with methylene chloride (4 times) and the. combined extracts were dried (Na2SO4) and evaporated to a yellow solid. The crude product was purified by chromatography on silica (chloroform/methanol gradient, 1-3% methanol) to give the title compound as a solid: 1H NMR (CDCl3) delta 8.34 (d, J=2.2 Hz, 1H), 8.88 (d, J=2.2 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 78473-10-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck & Co., Inc.; US6610692; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72093-04-0 , The common heterocyclic compound, 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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.

EXAMPLE 32 Compound CM A solution of diisopropylamine (1.23 mL)in dry tetrahydrofuran (15 mL) is stirred and cooled to -70 C. under a nitrogen atmosphere. To this is added a 2.5M solution of n-butyl lithium in hexanes (3.52 mL) at -70 C. The mixture is stirred for 30 minutes then a solution of 3-chloro-4-methylpyridine (1.02 g) in dry tetrahydrofuran (10 mL) is added. The mixture is stirred for a further 40 minutes. A solution of 3-cyclopentyloxy-4,N-dimethoxy-N-methylbenzamide (2.23 g) in dry tetrahydrofuran (10 mL) is added and the mixture stirred at -70 C. for 30 minutes, -40 C. for 30 minutes, 0 C. for 30 minutes, and room temperature for 1 hour. A mixture of ethanol and hydrochloric acid 19:1 (40 mL) is added and then the reaction mixture is partitioned between brine (40 mL) and diethyl ether (40 mL). The ethereal phase is dried over sodium sulfate and concentrated in vacuo to give a pale yellow solid (3.0 g). The solid is triturated with diethyl ether and then purified by flash chromatography (ethyl acetate eluent on a silica column) to give a solid (1.6 g). The solid is triturated with diethyl ether, collected and dried to afford 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(3-chloropyrid-4-yl)ethanone (1.35 g) as a cream solid m.p. 124-125 C. ?Elemental analysis: C,66.2; H,5.89; N,4.12%; calculated for C19 H20 ClNO3: C,65.99; H,5.83;[N,4.05%.]

The synthetic route of 72093-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer Limited; US5679696; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55899-13-3, Adding some certain compound to certain chemical reactions, such as: 55899-13-3, name is 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate,molecular formula is C14H17BrN2O3S, 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 55899-13-3.

In contrast to the other examples, only the cyclisation reaction was performed in flow. TheVapourtec R-series was equipped with three pumps. MSH 1 (2 g, 71 % damp solid, 6.60 mmol)1 and 3-bromopyridine 2a (1.04 g, 6.60 mmol) were dissolved together in THF/H2O (1:1, 33 mL, 0.2 M). Triethylamine (0.92mL, 6.60 mmol) dissolved in THF (8.25 mL, 0.8 M) was mixed with the first inlet via a Y-piece with flow rates of2.86 mL/min and 1.07 mL/min respectively (1.5 eq of triethylamine). Methyl propiolate 4a (0.56 g, 6.60 mmol) wasdissolved in THF (8.25 mL, 0.8 M) and introduced in a second Y-piece at flow rate 1.07 mL/min (1.5 eq of methylpropiolate). The system solvent was THF. The PFA reactor coils, with volumes 2 mL and 10 mL respectively, were setto temperatures 30 C and 90 C respectively. The reaction mixture from the first two inlet streams spent 31 secondsresidency time in the first reactor and then 2 minutes residency time in the second reactor. The operating pressure was7.5 bar with 3 pumps. The reaction set-up was flushed afterwards with 33 % HCl (conc.) in MeOH followed by IPA.The total flow rate at the outlet was 5 mL/min. The outlet stream (40 mL, collected over 8 minutes) was concentratedin vacuo to remove the THF and then diluted with EtOAc (250 mL) and brine (100 mL). The organic layer wasseparated and the aqueous phase washed twice more with EtOAc (2 x 200 mL). The combined organic layers weredried over anhydrous sodium sulfate and concentrated in vacuo to give a dark red oil.The crude material was purified by column chromatography on a 100 g silica column using the Biotage machine anda gradient from 7 to 60 % EtOAc/heptane. 5a eluted first from the column. Pale red solid (0.43 g, 8 min collectiontime, 42 %). 1H NMR (400 MHz, d6-DMSO) 4.10 (3H, s, CH3), 7.79 (1H, d, J = 8 Hz, ArH), 8.26 (1H, d, J = 8 Hz,ArH), 8.73 (1H, s, ArH), 9.56 (1H, s, ArH) ppm. 13C NMR (101 MHz, d6-DMSO) 51.2, 103.3, 108.1, 118.8, 130.3,131.4, 138.7, 144.6, 162.6 ppm. HRMS (FAB) calcd for C9H8O2N2Br 254.97637, found 254.97636/256.97421.5b eluted second from the column. Pale yellow solid. (0.14 g, 8 min collection time, 14 %). 1H NMR (400 MHz, d6-DMSO) 3.82 (3H, s, CH3), 7.06 (1H, dd, J = 4 and 4 Hz, ArH), 7.87 (1H, d, J = 4 Hz, ArH), 8.50 (1H, s, ArH), 8.93(1H, d, J = 4 Hz, ArH) ppm. 13C NMR (101 MHz, d6-DMSO) 51.3, 104.7, 109.8, 114.4, 129.8, 132.8, 137.6, 145.6,161.9 ppm. HRMS (FAB) calcd for C9H8O2N2Br 254.97637, found 254.97638/256.97424

According to the analysis of related databases, 55899-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brocklehurst, Cara E.; Koch, Guido; Rothe-Poellet, Stephanie; La Vecchia, Luigi; Synlett; vol. 28; 13; (2017); p. 1636 – 1640;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine. A new synthetic method of this compound is introduced below.

To a 10 mL microwave tube was added sodium tert-butoxide (0.105 mL, 0.856 mmol), [dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine]2-(2-aminoethyl)phenyl)palladium(II) chloride (15.54 mg, 0.019 mmol), 2-chloro-5-methoxy-pyridine (61.5 mg, 0.428 mmol), 1-(trans-3-aminocyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (intermediate 26, 90 mg, 0.389 mmol) and dry dioxane (1 mL) and it was sealed under argon. The mixture was stirred at 110 C. for 2 hours. The vial was opened and the reaction mixture evaporated to dryness under reduced pressure. Purification using reverse phase HPLC gave 1-(trans-3-(bis(5-methoxypyridin-2-yl)amino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (62 mg, 0.139 mmol, 35% yield). M+1: 446.1. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.35 (s, 6H) 2.47-2.61 (m, 2H) 3.20-3.33 (m, 2H) 3.83 (s, 6H) 4.97-5.14 (m, 1H) 5.20-5.33 (m, 1H) 6.83 (d, J=8.77 Hz, 2H) 6.92 (dd, j=7.16, 5.26 Hz, 1H) 7.17 (dd, J=8.84, 3.14 Hz, 2H) 7.39 (dd, J=7.16, 1.61 Hz, 1H) 8.10 (d, J=2.92 Hz, 2H) 8.17 (dd, J=5.26, 1.61 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem