Day: August 18, 2021

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.626-60-8, name is 3-Chloropyridine, molecular formula is C5H4ClN, molecular weight is 113.54, as common compound, the synthetic route is as follows.Application In Synthesis of 3-Chloropyridine

General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF?3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-60-8, 3-Chloropyridine, and friends who are interested can also refer to it.

Reference:
Article; Gu, Zheng-Song; Shao, Li-Xiong; Lu, Jian-Mei; Journal of Organometallic Chemistry; vol. 700; (2012); p. 132 – 134;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 624-28-2, 2,5-Dibromopyridine, 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, Product Details of 624-28-2, blongs to pyridine-derivatives compound. Product Details of 624-28-2

3.1. 1,1-dimethylethyl 4-(5-bromo-2-pyridyl)-1-piperazinecarboxylate 29.2 g (157 mmol) of 1,1-dimethylethyl 1-piperazine-carboxylate, 37 g (157 mmol) of 2,5-dibromopyridine and 21.7 g (157 mmol) of potassium carbonate suspended in 27 ml of dimethyl sulfoxide (DMSO) are introduced into an autoclave. The mixture is then heated at 150 C. for 21 hours. The reaction mixture is allowed to cool to room temperature, it is taken up in ethyl acetate and water and the insoluble material is then separated out by filtration. The aqueous phase is separated out and extracted twice with ethyl acetate, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel, eluding with a 99/1 mixture of dichloromethane and methanol. 44 g of product are thus obtained in the form of a white solid. m.p. ( C.): 83-85 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,624-28-2, 2,5-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2006/293310; (2006); 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.93-60-7, name is Methyl nicotinate, molecular formula is C7H7NO2, molecular weight is 137.136, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl nicotinate

A 10 l Buechi stirred autoclave with gas inlet tube, stirrer, internal thermometer and pressure equalizer was initially charged with 1.72 kg of methyl nicotinate (12.5 mol). 3.68 kg of diethylamine (50 mol) and 100 g of potassium tert-butoxide as a catalyst were slowly added thereto, and the mixture was homogenized while stirring.The reaction mixture thus obtained was pumped through the reaction tube continuously at 4 l/h at a working pressure of 30 bar and exposed to a microwave power of 2.8 kW, 91% of which was absorbed by the reaction mixture. The residence time of the reaction mixture in the irradiation zone was approx. 42 seconds. At the end of the reaction tube, the reaction mixture had a temperature of 285 C. Immediately after leaving the reactor, the reaction mixture was cooled to room temperature with a jacketed coil heat exchanger.A conversion of 85% of theory was attained. The reaction product was pale yellowish in color; the iron content was <5 ppm. After distillative removal of the methanol formed and of the excess or unconverted reactants, 1.85 kg of N,N-diethylnicotinamide with a purity of 98% were obtained by means of vacuum distillation. At the same time, in my other blogs, there are other synthetic methods of this type of compound,93-60-7, Methyl nicotinate, and friends who are interested can also refer to it. Reference:
Patent; CLARIANT FINANCE (BVI) LIMITED; US2012/95238; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929000-66-8, 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.929000-66-8, name is 3-Bromo-6-chloropyridine-2-carboxylic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.4505, as common compound, the synthetic route is as follows.

A mixture of 3-bromo-6-chloropyridine-2-carboxylic acid (10.0 g, 42.2 mmol, CAS 929000-66-8) in MeOH (100.0 mL)/SOCl2 (10.0 mL) was stirred at 80 C for 3 hours. The reaction mixture was concentrated in vacuo to give methyl 3-bromo-6-chloropyridine-2- carboxylate (10.4 g, 99% yield) as a yellow solid.

Statistics shows that 929000-66-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-chloropyridine-2-carboxylic acid.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); 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.60832-72-6, name is Oxazolo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4N2O2, molecular weight is 136.1082, as common compound, the synthetic route is as follows.COA of Formula: C6H4N2O2

Preparation 7 6-BROMO-3H-OXAZOLO[4,5-b]-PYRIDIN-2-ONE 0.01 mol of oxazolo[4,5-b]pyridin-2-one is dissolved in 100 ml of dimethylformamide. 0.011 mol of bromine is added via a dropping funnel. Stirring is maintained for 1 hour 30 minutes at room temperature and an ice/water mixture is added. The product is filtered off. It is washed with water. The product is dried. Yield: 90%. Melting point: 234 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Science et Organisation; US5084456; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 171178-46-4 , The common heterocyclic compound, 171178-46-4, name is 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid, molecular formula is C11H13ClN2O4, 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.

5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinic acid (Intermediate B) (4.27 g, 15 mmol, 1 equiv.) was added to a 500 mL two necked oven-dried round bottom flask equipped with a stirring bar and suspended in dichloromethane (187 mL, 0.08M) was added. 4-Dimethylamino pyridine (7.40 g, 60 mmol, 4 equiv.) was added at 22C resulting in an homogeneous solution. /V-(3-dimethylaminopropyl)-/V-ethylcarbodiimide (4.65 g, 30 mmol, 2 equiv.) was added at that temperature and the crude mixture was stirred for 3 h. Anhydrous MeOH (HPLC quality), (5.5 mL, 135 mmol, 9 equiv.) was added to the solution and the mixture was stirred for 1 h at 22C. The resulting mixture was heated to reflux using an aluminium heating block for 72 h. TLC (EtOAc:MeOH 90:10 %v/v) showed complete conversion of Intermediate B into Intermediate C. The reaction was permitted to reach to 22C and volatiles were removed under reduced pressure. Dichloromethane (150 mL) was added to the residue until complete solution was achieved and the mixture was transferred to a separating funnel, washed with H2O (1 x 70 mL), HCI 1 M (2 x 50 mL) and saturated NaCI solution (1 x 50 mL). The organic phase was dried with Na2S04 and filtered through a pad of Na2S04 on a filter plate. The solvent was removed under reduced pressure giving a brown solid, which was purified by automated flash chromatography (Heptane:EtOAc, product elution with EtOAc 100%v/v) giving methyl 5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinate as a pale yellow solid (4.04 g, 79% yield). Purity: 99.4% (UPLC-A); mp: 90.0-95.8 C; 1H- NMR (CDCI3), 5(ppm): 9.68 (bs, NH), 9.49 (s, 1 H), 7.73(s, 1 H), 7.20 (s, 1 H), 3.91 (s, 3H), 1.47 (s, 9H); LR-MS (ESI+): m/z= 287.1 Da [M+H]+, calcd. for CI2HI5CIN204: 286.2

The synthetic route of 171178-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAES FARMA, S.A.; HERNANDEZ HERRERO, Gonzalo; GARCIA DOMINGUEZ, Neftali; ZAZPE ARCE, Arturo; OLIVERA TIZNE, Roberto; NOVERGES PEDRO, Barbara; CORCOSTEGUI VIVAR, Reyes; TATO CERDEIRAS, Paloma; (124 pag.)WO2020/20939; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144100-07-2, 2-Bromo-6-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, Quality Control of 2-Bromo-6-fluoropyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-6-fluoropyridine

A solution of 2-bromo-6-fluoropyridine (2.4 g, 13.64 mmol), o-tolylboronic acid (2.039 g, 15.00 mmol) and Tetrakis (0.158 g, 0.136 mmol) in Dioxane was degassed by nitrogen bubble for 10 min. A solution of Phosphoric acid, potassium salt (8.68 g, 40.9 mmol) in H20 (2ml) was then added and the solution heated to reflux for 18 h. The crude material was purified via silica gel chromatography (90g SiOi column, hexane:EtOAc 100:0 -> 90: 10) to afford 2-fluoro-6-(o-tolyl)pyridine, 2.41 g (94percent). NuMuRhonu (400 MHz, CDCb) delta 7.87 (q, J=8.2 Hz, 1H), 7.46 – 7.41 (m, 1H), 7.37 – 7.26 (m, 4H), 6.92 (dd, J=8.2, 2.9 Hz, 1H), 2.43 (s, 3H).

The synthetic route of 144100-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16063-69-7, Adding some certain compound to certain chemical reactions, such as: 16063-69-7, name is 2,4,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 16063-69-7.

To a mixture of 2,4,6-trichloropyridine (5 g, 27.5 mmol. 1 eq), morpholine (7.2 mL, 82.3mmol, 3 eq), sodium tert-butoxide (7.9 g, 82.3 mmol, 3 eq), (2-biphenyl)di-tert-butyl-phosphine (408 mg, 2.7 mmol, 0.05 eq) in tetrahydrofuran (80 mL) was added Pd(dppf)C12 (from Combi-blocks, product number: OT-0746), 1 g, 2.7 mmol, 0.05 eq). The mixture was stirred at 8000 for 4 h. The mixture was cooled down to room temperature and poured onto a saturated solution of NH4CI (100 mL). The phases were separated and theaqueous phase was extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure using a rotary evaporator. Products Bi and B2 were isolated by flash chromatography on silica gel using first a 1:4.5 mixture of ethyl acetate and cyclohexane and then 1:1 mixture of ethyl acetate and cyclohexane as eluent. The product fractionswere pooled and evaporated to yield Bi as an off white powder (2.45 g, 8.6 mmol, 31%)and B2 as an off white powder (2.2 g, 7.8 mmol, 28% 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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITAET BASEL; PIQUR THERAPEUTICS AG; HEBEISEN, Paul; BEAUFILS, Florent; LANGLOIS, Jean-Baptiste; WO2015/162084; (2015); 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.1970-81-6, name is [3,3′-Bipyridine]-5-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.Recommanded Product: 1970-81-6

Referring to Scheme 1, synthesis of compound 13, to a cooled (0C) suspension of compound 2 (0.6 g, 3.0 mmol) in dichloromethane (100 mL), was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.69 g, 3.6 mmol), 1-hydroxy-benzotriazole hydrate (0.49 g, 3.6 mmol), and triethylamine (0.5 mL, 3.6 mmol). After stirring for 30 min. at 0C (the reaction became almost clear), compound 9 (0.4 g, 1.2 mmol) and triethylamine (1.0 mL, 7.2 mmol) were added. The reaction was stirred for 16 h., then washed with saturated NaHCO3 (3 x 50 mL). The DCM layer was dried with MgSO4, reduced in volume in vacuo, and purified by flash column chromatography (2% – 25% methanol in DCM) to give compound 13 (90 mg, 12%). 1H NMR (CDCl3, 500 MHz) delta 1.70 (m, 2H), 1.75 (m, 2H), 1.87 (m, 2H), 1.89 (s, 3H), 1.98 (m, 1H), 2.14 (m, 1H), 3.28 (m, 1H), 3.35 (m, 1H), 3.40 (m, 2H), 3.64 (m, 1H), 3.70 (m, 1H), 4.85 (q, J = 4.9 Hz, 1H), 5.30 (s, 1H), 5.67 (s, 1H), 6.40 (t, J = 5.0 Hz, 1H), 7.36 (t, J = 5.0 Hz, 1H), 7.42 (dd, J = 3.9, 2.2 Hz, 1H), 7.43 (dd, J = 3.9, 2.2 Hz, 1H), 7.65 (t, J = 4.45 Hz, 1H), 7.72 (d, J = 6.1 Hz, 1H), 7.93 (d, J = 1.5 Hz, 1H), 7.95 (d, J = 1.5 Hz, 1H), 8.42 (m, 2H), 8.67 (dd, J = 4.1, 1.0 Hz, 1H), 8.68 (dd, J = 4.0, 1.2 Hz, 1H), 8.889 (s, 1H), 8.891 (s, 1H), 8.93 (d, J = 1.7 Hz, 1H), 8.96 (d, J = 1.8 Hz, 1H), 9.10 (d, J = 1.6 Hz, 1H), 9.13 (d, J = 1.7 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1970-81-6, [3,3′-Bipyridine]-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MEDTRONIC MINIMED, INC.; GAMSEY, Soya; WESSLING, Ritchie, A.; EP2222686; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6271-78-9, 6-Chloropyridine-3-carboxamide, 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, Quality Control of 6-Chloropyridine-3-carboxamide, blongs to pyridine-derivatives compound. Quality Control of 6-Chloropyridine-3-carboxamide

A solution of 6-chloronicotinamide (15 g, 95.8 mmol) and hexamethyleneimine(11.4 g, 115 mmol) in DMSO (20 mL) was heated at 60 oC for 12 hours afterwhich TLC indicate complete consumption of the starting material. The mixturewas diluted with water which resulted in the formation of a thick precipitate andrequired further dilution to give a free-flowing mixture to filter (300 mL water).The solid was filtered off and washed with water (50 mL). The solid wasdissolved in DCM (500 mL) and EtOAc (500 mL), dried (Na2SO4), filtered, andconcentrated in vacuo. The resulting solid was suspended in EtOAc and filteredto give 13 as a beige crystalline solid (12 g, 57%).1H NMR (400 MHz, DMSO-d6): delta 1.4 – 1.5 (m, 4H), 1.6 – 1.7 (m, 4H), 3.5 – 3.7(m, 4H), 6.6 (d, J = 9.2 Hz, 1H), 7.0 (br s, 1H), 7.6 (br s, 1H), 7.9 (dd, J = 2.4 Hz,J = 9.2 Hz, 1H), 8.5 (d, J = 2.4 Hz, 1H). 13C NMR (100 MHz, DMSO-d6): delta 26.8,27.4, 47.6, 104.5, 117.2, 137.0, 149.0, 159.3, 167.5. MS (ESI) m/z: [M – H]+Calculated for C12H16N3O: 218.27; Found: 218.4. Purity: >99.0%.

The synthetic route of 6271-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jalily, Pouria H.; Eldstrom, Jodene; Miller, Scott C.; Kwan, Daniel C.; Tai, Sheldon S.-H.; Chou, Doug; Niikura, Masahiro; Tietjen, Ian; Fedida, David; Molecular Pharmacology; vol. 90; 2; (2016); p. 80 – 95;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem