Day: September 17, 2021

Application of 874-80-6 ,Some common heterocyclic compound, 874-80-6, molecular formula is C9H14BrN, 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.

General procedure: Tributyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide [P44414][NTf2] (1); 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide [BMMIM][NTf2] (3); 1-butylpyridiniumbis(trifluoromethylsulfonyl)imide [BuPy][NTf2] (2); 1-allylpyridinium bis(trifluoromethylsulfonyl)imide[AllPy][NTf2] (5); 1-allyl-2,3-dimethylimidazoliumbis(trifluoromethylsulfonyl)imide [AlldiMIM][NTf2] (7)and 1,3-diallyl-2-methylimiidazolium bis(trifluoromethylsulfonyl)imide [diAllMIM][NTf2] (6) weresynthesized by metathesis reaction using the general procedure:Pyridinium or imidazolium halide (bromide or chloride) was dissolved in water and it wastransferred to a separator funnel with dichloromethane. Subsequently, 1.1 molar equivalent of LiNTf2(80% solution in water) was added and a separator funnel was shaken vigorously. After phaseseparation, the organic phase was washed twice with water, once with 5% water solution of LiNTf2,and this procedure was repeated until water phase was completely free of halide anion. To confirmabsence of chloride anion, acidic solution of silver nitrate was added to a sample of water phase. Noprecipitate of silver chloride indicated an absence of chloride anion. Subsequently, the organic phasewas separated, evaporated and dried under high vacuum (1 mbar) in 60 C for 24 h. The structure ofobtained salts were confirmed by 1H-NMR analysis.

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. 874-80-6, N-butylpyridinium bromide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zielinski, Witold; Kukawka, Rafal; Maciejewski, Hieronim; Smiglak, Marcin; Molecules; vol. 21; 9; (2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89167-19-1, 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 89167-19-1, name is 3-Bromo-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-Bromo-4-iodopyridine (2.2 g, 7.8 mmol), 2-Methoxyphenylboronic acid (1.3 g, 8.6 mmol), sodium carbonate (1.7 g, 15.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) were charged and vessel evacuated and purged with nitrogen. Added nitrogen degassed 3:1 solution of dioxane and water (15 ml) and reaction heated to 100C for 2 hrs. Reaction was partitioned between EtOAc and water. The organics were washed with brine, dried and concentrated. The crude product was purified by flash column using a gradient of 100% Hexanes to 1:1 Hexanes and EtOAc to isolate the product as a glassy solid. LC-MS m z: 264 [M+l]

According to the analysis of related databases, 89167-19-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; SHAH, Shrenik, K.; KURUKULASURIYA, Ravi; FUNG, Selena; COLANDREA, Vincent, J.; SZEWCZYK, Jason, W.; WO2013/62887; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58584-86-4, 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. 58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, 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.

Ethyl 2,6-dichloropyridine-3-carboxylate (7.00 g, 31.81 mmol) and (6-isopropoxy-3-pyridyl)boronic acid (5.04 g, 27.85 mmol) were combined and dissolved in ethanol (50.40 mL) and toluene (50.40 mL). A suspension of sodium carbonate (10.12 g, 95.47 mmol) in water (10.08 mL) was added. Under nitrogen, tetrakis(triphenylphosphine)palladium (1.103 g, 0.9547 mmol) was added. The reaction mixture was allowed to warm to 80 C. and stirred for 2 h. The volatiles were removed under reduced pressure. The remaining solids were partitioned between water (75 mL) and ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium chloride solution (1×75 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The material was subjected to silica gel column chromatography using a gradient from 100% hexanes to 5% ethyl acetate in hexanes. Ethyl 2-chloro-6-(6-isopropoxy-3-pyridyl)pyridine-3-carboxylate (3.95 g, 12.07 mmol, 43.33%) was obtained as a clear colorless oil. 1H NMR (400 MHz, DMSO) delta 8.91 (s, 1H), 8.37 (dd, J=8.7, 2.3 Hz, 1H), 8.30 (d, J=8.1 Hz, 1H), 8.10 (d, J=8.1 Hz, 1H), 6.89 (d, J=8.7 Hz, 1H), 5.34 (dt, J=12.3, 6.1 Hz, 1H), 4.36 (q, J=7.1 Hz, 2H), 2.51 (d, J=1.7 Hz, 1H), 1.42-1.30 (m, 9H). ESI-MS m/z calc. 320.09277. found 321.2 (M+1)+. Retention time: 0.72 minutes.

According to the analysis of related databases, 58584-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); 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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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. Application In Synthesis of 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.3 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-pent-4-enoate (S)-Enantiomer, ((S)-15): Yield: 750 mg (55%), white solid. Mp 176-177 C. 1H NMR (300 MHz, CDCl3): delta 1.31 (s, 9H), 2.27 (ddd, 2JH,H = 14.7 Hz, 3JH,H = 8.0 Hz, 3JH,H = 6.9 Hz, 1H), 2.49 (dt, 3JH,H = 13.8 Hz, 3JH,H = 6.9 Hz, 1H), 3.86 (s, 3H), 4.49 (d, 2JH,H = 16.1 Hz, 1H), 4.51 (t, 3JH,H = 7.5 Hz, 1H), 4.69 (d, 2JH,H = 16.6 Hz, 1H), 4.89 (dd, 3JH,H = 17.1 Hz, 2JH,H = 1.5 Hz, 1H), 4.99 (dd, 3JH,H = 10.2 Hz, 2JH,H = 1.5 Hz, 1H), 5.60 (ddt, 3JH,H = 17.0 Hz, 3JH,H = 10.3 Hz, 3JH,H = 6.7 Hz, 1H), 6.94 (dm, 3JH,H = 9.0 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.9 Hz, 1H), 7.73 (dm, 3JH,H = 9.0 Hz, 2H), 7.86 (d, 3JH,H = 7.9 Hz, 1H), 8.50 (d, 3JH,H = 4.0 Hz, 1H), 8.54 (d, 4JH,H = 1.7 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.8 (q), 35.5 (t), 46.6 (t), 55.6 (q), 60.2 (d), 82.3 (s), 114.1 (d), 118.4 (t), 123.3 (d), 129.6 (d), 131.5 (s), 133.0 (d), 133.7 (s), 136.6 (d), 148.5 (d), 149.0 (d), 163.0 (s), 169.3 (s) ppm. HRMS (ESI+): C22H28N2O5S+H+, calcd 433.1797, found: 433.1812; C22H28N2O5S + Na+, calcd 455.1617, found: 455.1630, (C22H28N2O5S)2+H+, calcd 865.3516, found: 865.3532; (C22H28N2O5S)2 + Na+, calcd 887.3336, found: 887.3345. Optical rotation (c 1.001, CHCl3): [alpha]58920 = -26.4, [alpha]57820 = -27.3, [alpha]54620 = -31.2, [alpha]43620 = -56.6, [alpha]36520 = -97.7.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69627-02-7, 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.69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, molecular weight is 151.19, as common compound, the synthetic route is as follows.

5.00 g of [3,2-b]pyridin-7-ol (33 mmol) and 50 g of phosphorus oxybromide (174 mmol) are put in a flask and heated at 1100C for 3h. The hot reaction mixture is poured into mixture of ice and 5N NaOH and extracted with CHC12, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane :AcOEt=3:l) to give 4.19 g of the title compound . Yield 59%. mass spectrum (m/e):215(M+l); IH-NMR(CDCl3): 8.55(d, IH, J=4.3Hz), 7.86(d, IH, J=5.7Hz), 7.69(d, IH, J=5.7Hz), 7.49(d, IH, J=4.3Hz) ppm.

Statistics shows that 69627-02-7 is playing an increasingly important role. we look forward to future research findings about Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/107784; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-29-0, 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 504-29-0, name is Pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 47 pyridine-2-amino-5-sulphonic Acid 2-Aminopyridine (80 g, 0.85 mol) was added portionwise over 30 minutes to oleum (320 g) and the resulting solution heated at 140 C. for 4 hours.. On cooling, the reaction was poured onto ice (200 g) and the mixture stirred in an ice/salt bath for a further 2 hours.. The resulting suspension was filtered, the solid washed with ice water (200 ml) and cold IMS (200 ml) and dried under suction to afford the title compound as a solid, (111.3 g). LRMS: m/z 175 (M+1)+.

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6407114; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 771579-27-2, 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. 771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, molecular formula is C8H12N2O, 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.

Carboxylic acid (13.44g, 39.4mmol) was dissolved in 70mLDMSO, and added with stirring 4,6-dimethyl-3-aminomethyl-pyridinePyridine -2 (1H) – one (12.4g, 81.9mmol). Stirred at room temperature 15min, then add hexafluorophosphate, benzotriazol-1-yl – yloxy tripyrrolidinophosphonium phosphorus (PYBOP) (31.9g, 61.4mmol), stirred at room temperature overnight, until the reaction was complete (developing solvent: ethyl acetate / ethanol = 5: 1), the reaction mixture was poured into 700mL ice water, stirred for 30min, to obtain a solid by suction filtration, washed with a 500 mL of water, and dried under vacuum dryer, the resulting solid was added with stirring acetonitrile (75mL × 2), suction, vacuum dryer. The resulting solid was combined with 100mL stirring methanol / dichloromethane (5:95), filtration, and dried under reduced pressure to obtain a solid product was thoroughly 14g, Yield 74%

According to the analysis of related databases, 771579-27-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu University of Technology; Liang, Guoping; Wang, Yazhen; Zheng, Chunzhi; Zhao, Dejian; Zhang, Jizhen; (13 pag.)CN105440023; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98549-88-3, 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.98549-88-3, name is 1H-Pyrrolo[2,3-b]pyridin-5-ol, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

Example 724-[4-(1H-Pyrrolo[2,3-b]pyridin-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol), 1H-pyrrolo[2,3-B]pyridin-5-ol (Matrix Scientific, Columbia, S.C., USA; 26 mg, 0.19 mmol), and potassium carbonate (27 mg, 0.19 mmol) in dimethylformamide (2 mL) was heated in the microwave oven at 160 C. for 10 min. Ethyl acetate and water were added, and the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted twice with dichloromethane and the solvent was evaporated under high vacuum to give 4-[4-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (21 mg, 33%) as a white powder. 1H NMR (300 MHz, DMSO-d6) delta 1.43 (s, 9H), 1.80-2.15 (m, 4H), 3.02 (br s, 2H), 4.08 (d, 2H, J=12.4 Hz), 4.85-5.10 (m, 1H), 6.45-6.52 (m, 1H), 7.58 (d, 1H, J=2.9 Hz), 7.94 (d, 1H, J=2.5 Hz), 8.20 (d, 1H, J=2.5 Hz), 8.22 (s, 1H), 8.50 (s, 1H), 11.85 (br s, 1H). Mass spectrum (ES) MH+=436. HRMS Calcd. for C22H26N7O3 (MH+): 436.2092. Found: 436.2090.

The chemical industry reduces the impact on the environment during synthesis 98549-88-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); 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. 1990-90-5, name is 3-Methylpyridin-4-amine, the common compound, a new synthetic route is introduced below. COA of Formula: C6H8N2

To a solution of 2-(5-chloro-2-fluorophenyl)-4-iodo-5-methyl-6,7-dihydro-5H-cyclo- pentapyrimidine (275 mg, 0.71 mmol, 1 eq) in dioxane (5 ml) was added Pd(OAc)2 (8 mg, 0.04 mmol, 0.05 eq) followed by BINAP (33 mg, 0.05 mmol, 0.075 eq), 4-amino-3-picoline (84 mg, 0.78 mmol, 1.1 eq) and Cs2CO3 (347 mg, 1.06 mmol, 1.5 eq). The reaction mixture was heated to 80C for 15 h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by flash column chromatography (l:l/ethyl acetate:hexane-100% ethyl acetate) to afford [2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl]- (3-methyl-pyridin-4-yl)-amine, compound of formula (43) (250 mg, 96%)

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 889865-45-6, 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.889865-45-6, name is 2,3-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, molecular weight is 273.89, as common compound, the synthetic route is as follows.

Compound N13z (135 mg, 318 mmol) in 1,4-dioxane (3 mL) was added Pd2(dba)3 (14.5 mg, 0.0159 mmol), XantPhos (18.4 mg, 0.0318 mmol), 2,3-dichloro-4-iodopyridine (109 mg, 0.397 mmol), and DIPEA (0.166 mL, 0.954 mmol). The reaction vessel was purged with argon, sealed, and heated to 110 C. until complete consumption of starting materials. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water followed by brine. The organic partition was dried over magnesium sulfate, and filtered through Celite. The resulting solution was concentrated and purified by column chromatography (0-100% EtOAc in hexanes). This provided Compound E46a. LCMS ESI+ calc’d for C25H30Cl2N6O2S: 549.2 [M+H+]. found: 549.2 [M+H+].

Statistics shows that 889865-45-6 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloro-4-iodopyridine.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Gregory; Clarke, Michael O’ Neil Hanrahan; Han, Xiaochun; Hansen, Tim; Hu, Yunfeng Eric; Koltun, Dmitry; McFadden, Ryan; Mish, Michael R.; Parkhill, Eric Q.; Sperandio, David; Xu, Lianhong; Yang, Hai; (199 pag.)US2020/108071; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem