Tag: M.W=300-400

Synthetic Route of 153747-97-8 , The common heterocyclic compound, 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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.

Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (2.0 g, 5.84 mmol),Bis(boronic acid) pinacol ester (2.2 g, 8.77 mmol) andPotassium acetate (1.72 g, 17.53 mmol)To a solution of dimethyl sulfoxide (10 mL) was added Pd(dppf)Cl2.CH2Cl2 (473.0 mg, 0.58 mmol).The reaction was heated to 80C and stirred for 2 hours.Cool toDiluted with ethyl acetate (100 mL) at room temperature and filtered through celite. The filtrate was washed with saturated brine (100 mL x 4), anhydrousSodium sulfate was dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 3/1) to give the title compoundThe product was an off-white solid (2.55 g, 112%).

The synthetic route of 153747-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53710-18-2, 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. 53710-18-2, name is 3,5-Diiodopyridine. A new synthetic method of this compound is introduced below.

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4,filtered and concentrated in vacuo to give a crude product, which was purified by silica gelflash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g,45%) as a light yellow solid. MS: 399.2 (M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53710-18-2, 3,5-Diiodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59020-10-9 ,Some common heterocyclic compound, 59020-10-9, molecular formula is C17H31NSn, 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.

34a. 5-(3-Pyridinyl)-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine (from Example 23a, 500 mg, 1.28 mmol) in toluene (10.0 mL) was added 3-pyridinyltributyltin (564 mg, 1.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.039 mmol). After being refluxed overnight, the resulting mixture was cooled to room temperature. Solvent was removed and the residue was chromatographed on a silica gel column, eluding with hexane/EtOAc 2:1 and 1:1 to afford an oil (428 mg, 86%). MS (CI/NH3) m/z 390 (M+H)+. 1H NMR (CDCl3, 300 MHz) delta 1.24-1.67 (m, 2H), 1.44 (s, 9H), 1.86-2.10 (m, 2H), 3.32-3.45 (m, 2H), 3.95-4.27 (m, 3H), 7.28-7.44 (m, 2H), 7.81-7.86 (m, 1H), 8.14-8.17 (m, 1H), 8.65-8.73 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59020-10-9, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6437138; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153747-97-8, Adding some certain compound to certain chemical reactions, such as: 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate,molecular formula is C14H20BrN3O2, 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 153747-97-8.

[0951] A solution ofcompound 90b (125 g, 366 mmol) inDMF (1.30 L)was treatedwith, 4,4,4′,4′,5,5,5′,5′-octamethyl2,2′-bi(1,3,2-dioxaborolane) (186 g, 732 mmol), Pd(OAc) 2(4.09 g, 18.3 mmol), PPh3 (19.2 g, 73.2 mmol) and KOAc(108 g, 1.10 mol) under a nitrogen atmosphere. The resultingmixture was stirred overnight at 80 C. Upon cooling to roomtemperature, the solids were collected by filtration. The filtrate was concentratedunderreduced pressure, and the resultant residue was purified by flash colunm chromatography onsilica gel (EtOAc/petroleum ether (1 :50 v/v)) to obtain compound 90c as a white solid (80.0 g, 56% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H32BN3 0 4 : 390.2(M+H). found 390.2.

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188425-85-6, 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. 188425-85-6, name is 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide, molecular formula is C18H12Cl2N2O, 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.

Compound 2-chloro-N-(4′-chloro-5-hydroxybiphenyl-2-yl)nicotinamide, which is the main metabolite of boscalid, was prepared following the synthetic scheme depicted in Fig. 1. Briefly, phenyliodine(III) bis(trifluoroacetate) (PIFA, 451 mg, 1.049 mmol, 1.2 equiv) was added to a solution of boscalid (300 mg, 0.875 mmol) and trifluoroacetic acid (673 muL, 7.4 mmol, 10 equiv) in CHCl3 (11.5 mL). After stirring for 3 h at room temperature, the reaction mixture was cooled in an ice bath and then quenched by the addition of 5% NaHCO3 (30 mL). The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and dried over anhydrous MgSO4. The brownish residue left after evaporation of the solvent was purified by column chromatography, using CHCl3/CH3OH 99:1 as eluent, to afford metabolite M510F01. IR vmax/cm-1 (NaCl) 3377, 3230, 3028, 1652, 1580, 1394, 1088, 1012, 749; 1H NMR (300 MHz, CDCl3) delta 8.42 (1H, dd, J = 4.8, 1.8 Hz, H-6 Py), 8.03 (1H, dd, J = 7.8, 1.8 Hz, H-4 Py), 7.99 (1H, br s, NH), 7.82 (1H, d, J = 8.7 Hz, H-3 PhPh), 7.38-7.23 (5H, m, H-2’/H-6′, H-3’/H-5′ and H-5 Py), 6.81 (1H, dd, J = 8.7, 3 Hz, H-4 PhPh), 6.72 (1H, d, J = 3 Hz, H-6 PhPh); 13C NMR (75 MHz, CDCl3) delta 163.44 (CON), 154.17 (C-5 PhPh), 151.24 (C-6 Py), 146.85 (C-2Py), 139.82 (C-4 Py), 136.22 (C-3 Py), 135.73 (C-10), 134.27 (C-4’PhPh), 130.89 (C-2 PhPh), 130.41 (C-3’/C-5′ PhPh), 129.02 (C-2’/C-6′ PhPh), 126.13 (C-1 PhPh), 125.69 (C-5 Py), 122.88 (C-2 PhPh), 117.16 (C-4 PhPh), 115.71 (C-6 PhPh); HRMS (TOF MS), calculated for C18H1135Cl2N2O2 [M-H]+ 357.0198, found 357.0219.

According to the analysis of related databases, 188425-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Esteve-Turrillas, Francesc A.; Mercader, Josep V.; Agullo, Consuelo; Abad-Somovilla, Antonio; Abad-Fuentes, Antonio; Food Chemistry; vol. 267; (2018); p. 2 – 9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 79491-46-6 ,Some common heterocyclic compound, 79491-46-6, molecular formula is C6H4Br2N2O3, 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.

Alternate procedures useful for the synthesis of Compound 39 Preparation of 5,7-dibromo-4-methoxy-7-azaindole 36: Vinylmagnesium bromide (0.85 M in THF, 97.7 mL, 83.0 mmol) was added over 30 min. to a stirring solution of 2,6-dibromo-3-methoxy-5-nitropyridine (7.4 g, 23.7 mmol) in THF (160 mL) at -75 C. The solution was stirred 1 h at -75 C., overnight at -20 C., recooled to -75 C. and quenched with saturated aqueous NH4Cl (~100 mL). The reaction mixture was allowed to warm to rt, washed with brine (-100 mL) and extracted with Et2O (150 mL) and CH2Cl2 (2*100 mL). The combined organics were dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography (SiO2, 3:1 hexanes/EtOAc) to yield 5,7-dibromo-4-methoxy-7-azaindole 36 (1.10 g, 3.60 mmol, 15%) as a pale yellow solid.

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. 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wang, Tao; Wallace, Owen B.; Zhang, Zhongxing; Meanwell, Nicholas A.; Bender, John A.; US2002/61892; (2002); 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. 847406-13-7, name is Ethyl 1-(5-bromopyridin-3-yl)piperidine-4-carboxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 847406-13-7

To a flask was added 7A (1. 00 G, 3.19 MMOL), DIOXANE (13 ML), triethyl AMINE (0. 97 g, 9. 58 mmol) and pinacol borane (0. 613 G., 4. 79’mmol). The mixture was degassed with N2 for 15 min and Pd2Cl2- (dppf) dcm (0.132 g, 0.16 mmol) was added. The flask was heated to 90C for 12 h and cooled to ambient temperature. The crude product was concen- rated in vacuo and purified by flash chromatography on silica gel eluting with 15% 7N methanolic ammonia/CM to provide the title compound (400 mg, 45%) 1H NMR (DMSO-d6, 400 MHz) 5 8.31 (d, J=2.73 Hz, 1H), 8.09 (m, 1H), 7.18 (m, 2H), 4.16 (dd, J=7.02, 14.04 Hz, 2H), 3.67 (m, 2H), 2. 85 (m, 2H), 2.46 (m, 1H), 2.05 (m, 2H), 1.89 (m, . 2H), 1.28 (t, J=7. 21 HZ,. 3H).

The synthetic route of 847406-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOS CORPORATION; WO2005/19200; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153747-97-8, 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.

Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (202 mg, 0.59 mmol),N,N-bis(tert-butoxycarbonyl)-3-(1-(2,5-dichlorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3) ,2-Dioxaborolan-2-yl)pyridin-2-amine (300 mg, 0.49 mmol) andCesium carbonate (320mg, 0.98mmol)Ethylene glycol dimethyl ether/water (10 mL/1 mL)Pd(dppf)Cl2.CH2Cl2 (40 mg, 0.05 mmol) was added to the mixture.The reaction solution is heated to 90C.After stirring overnight, cool to room temperature and filter through celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 5/1) to give the title compound as a yellow oil (250 mg, 68%).

Statistics shows that 153747-97-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55899-13-3 ,Some common heterocyclic compound, 55899-13-3, molecular formula is C14H17BrN2O3S, 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.

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

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. 55899-13-3, 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate, other downstream synthetic routes, hurry up and to see.

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

Application 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.

Methyl 6-bromo-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate [0424] A 70% perchloric acid aqueous solution (12.9 mL) was added to a 1,4-dioxane solution (31 mL) of ethyl O-mesitylsulfonylacetohydroxamate (35.7 g) under an argon atmosphere under ice-cooling, and then the mixture was stirred for 30 minutes under ice-cooling. Ice water (360 mL) was added to the reaction solution, the precipitated solid was filtered off, the obtained solid was dissolved in dichloromethane (104 mL), and the solution was divided into layers. The organic layer was dried over anhydrous magnesium sulfate and filtered off. A dichloromethane solution (104 mL) of 3-bromopyridine (10 mL) was added to the obtained filtrate under ice-cooling, the mixture was stirred at room temperature for 1 hour, and the reaction solution was evaporated to obtain a crude product N-amino-3-bromopyridinium 2,4,6-trimethylbenzenesulfonate. Methyl phenylpropiolate (7.7 mL) and potassium carbonate (28.7 g) were added to an N,N-dimethylformamide solution (104 mL) of the crude product N-amino-3-bromopyridinium 2,4,6-trimethylbenzenesulfonate at room temperature under an argon atmosphere, and then the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was evaporated and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 4:1) to obtain a title compound as a yellow powder (8.0 g).

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. 55899-13-3, 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; Kissei Pharmaceutical Co., Ltd.; SETO, Shigeki; UMEI, Kentaro; NISHIGAYA, Yosuke; TANIOKA, Asao; KONDO, Tatsuhiro; KONDO, Atsushi; TATANI, Kazuya; KAWAMURA, Naohiro; EP2669285; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem