Tag: M.W=300-400

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 59020-10-9, name is 3-(Tributylstannyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 59020-10-9

Example 54 (Sp) -8-(3-Pyridinyl)adenosine-2’O-(tert- butyldimethylsilyl)-3′,5′-cyclic N-phenylphosphoramidate (5j); A mixture of Pd (OAc)2 0.166 mmol) and PPh3 (91mg, 0.348 mmol) in NMP (4 ml) was stirred at 50 C until the solution had turned dark red. A solution of (Sp)-8- bromoadenosine-2’O-(tert-butyldimethylsilyl)-3′,5′-cyclic N-phenylphosphoramidate (4) (0.500 g, 0.83 mmol) in NMP (2 ml) and 3- (tributylstannyl)pyridine g, 1.66 mmol) were added. The reaction mixture was stirred at 110 C for 10 h before the NMP was removed at reduced pressure and the residual material subjected to flash chromatography on silica gel using 7.5% MeOH in CH2Cl2. The product was a white solid contaminated with traces of organotin residues which were removed by dissolution of the the coupling product in CH2Cl2 and reprecipitation by hexane; yield 0.280 g (57%); HRMS (electrospray) : M+H 596.2211. Calc. for C27H34N7O5PSi+H: 596.2201. ¹H NMR (CDC1,, 300 MHz) : No. (CDCl3)-0.16 (3H, s, CH3),-0.15 (3H, s, CH,) , 0.60 (9H, s, C(CH3)3) , 4.30 – 4.43 (lH, m, H-4′), 4.60 – 4.68 (2H, m, OCH,), 5.15 (lH, d, J 5.2 Hz, H-2′), 5.69 (lH, s, H-1′), 5.75 – 5.82 (lH, m, H-3′), 6.37 (2H, bs, NH2), 6.58 (lH, d, J 9.2 Hz, NH), 6.99 – 7.10 (3H, m, 3 x H-Ph), 7.17 – 7.24 (2H, t, J 7.4 Hz, 2 x H-Ph), 7.42 – 7.48 (lH, m, H-pyr), 8.02 – 8.06 (lH, m, H-pyr), 8.37 (lH, s, H-2), 8.76 – 8.79 (lH, m, H-pyr), 8.97 (lH, d, J 1.7 Hz, H-pyr); ¹3C NMR (CDCl3,75 MHz) : 8 -5.5 and -4.8 (2 x CH3) , 18. 0 (Si-C), 25.4 (3 x CH3), 68.9 (d, J 6.8 Hz, OCH,), 71.3 (d, J 4 .5 Hz, CH-4′), 73.3 (d. J 8.8 Hz, CH-2′), 77.5 (d, J 3.8 Hz, CH-3′), 94.2 (CH-1′), 119.4,119.5, 119.6,122.9, 123.5, 125.0,129.1, 129.1,136.8, 138.5,148.1, 149.8,150.3, 151.4,153.5, 155.9.

With the rapid development of chemical substances, we look forward to future research findings about 59020-10-9.

Reference:
Patent; LAURAS AS; COCKBAIN, Julian; WO2005/123755; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 877060-48-5 , The common heterocyclic compound, 877060-48-5, name is tert-Butyl 3-iodo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, molecular formula is C12H13IN2O2, 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.

1.1 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II)chloride and 15 mg (0.08 mmol) of copper(I)iodide are added to a solution, kept under nitrogen, of 1.37 g (4.00 mmol) of tert-butyl 3-iodopyrrolo[3,2-c]pyridine-1-carboxylate (prepared by the method of M. Lefoix et al, Synthesis, 2005, 20, 3581-3588) in 20 ml of tetrahydrofuran. Carbon monoxide is passed into this solution in an autoclave apparatus, and the mixture is stirred at a pressure of about 5 bar for 50 minutes. The apparatus is decompressed, 589 mg (6.00 mmol) of trimethylsilylacetylene and 405 mg (4.00 mmol) of triethylamine are added under nitrogen. The apparatus is re-pressurised to 5.8 bar with carbon monoxide, and the reaction mixture is stirred at room temperature for 45 hours. Saturated sodium chloride solution is added to the reaction mixture, which is then extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent: tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate as yellowish crystals; ESI 343.1.2 104 mg (0.75 mmol) of potassium carbonate are added to a solution of 103 mg (0.30 mmol of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate and 148 mg (0.75 mmol) of phenylguanidine carbonate in 1.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 68 hours. After cooling, 10 ml of water are added, and the mixture is stirred at 40 C. for 1 h. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving phenyl-[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]amine (?A1?) as pale-brown solid; ESI 287;1H NMR (DMSO-d6) delta [ppm] 6.90 (t, J=7.5 Hz, 1H), 7.25 (m, 3H), 7.39 (d, J=5.5 Hz, 1H), 7.76 (d, J=7.5 Hz, 2H), 8.22 (d, J=5.5 Hz, 1H), 8.32 (d, J=5.5 Hz, 1H), 8.35 (s, 1H), 9.46 (s, 1H), 9.81 (s, 1H), 12.0 (bs, 1H).

The synthetic route of 877060-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT; US2011/92527; (2011); 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.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.Quality Control of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

[0957] Into a 2 L 4-necked round-bottom flask, purged andmaintained with an inert atmosphere ofnitrogen, was placeda solution of compound 90e (42.8 g, 206 mmol) in 1,4-dioxane (1 L), compound 90b (80.0 g, 206 mmol), Pd(dppf)Cl2 (7.53 g, 10.3 mmol) andCs 2C0 3 (167 g, 514 mmol). Thereaction mixture was stirred overnight at 90 C. Upon cooling, the reaction was quenched with water (100 mL). Theresulting mixture was extracted with DCM. The combinedorganic layers were dried over Na2S04 , filtered and concentrated underreduced pressure. The resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (1 00:3 v/v)) to obtain compound 90fas a yellow solid(23.0 g, 29% yield). Mass Spectrum (LCMS, ESI pos.):Calcd. for C18H23ClN60 2 : 391.2 (M+H). found 391.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

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

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. 59020-10-9, name is 3-(Tributylstannyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C17H31NSn

147a. 6-Chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-5-(3-pyridyl)pyridine To a solution of 3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloropyridine (500 mg, 1.28 mmol) in toluene (10 mL) was added 3-pyridinyltributyltin (564 mg, 1.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.04 mmol). After being heated under reflux for 16 h, the resulting mixture was cooled to room temperature. Solvent was removed, and the residue was chromatographed (silica gel; EtOAc/hexane, 2:19 to 1:1) to afford an oil (428 mg, 86%): 1 H NMR (CDCl3, 300 MHz) delta1.45 (s, 9H), 1.94 (m, 1H), 1.98-2.10 (m, 2H), 3.31-3.45 (m, 2H), 3.88-4.30 (m, 4H), 7.22 (m, 1H), 7.40 (m, 1H), 7.83 (td, 1H, J=1.5, 9.0 Hz), 8.16 (d, 1H, J =3.0 Hz), 8.64-8.73 (m, 2H); MS (CI/NH3) m/z 390 (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, 59020-10-9, 3-(Tributylstannyl)pyridine.

Reference:
Patent; Abbott Laboratories; US6127386; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3IN, 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.

Step D 3-chloro-2-iodo-6-(trifluoromethyl)pyridine Into a 100 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (as prepared in the previous step, 2 g, 6.51 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of LDA (730 mg, 6.82 mmol, 1.05 equiv, as a THF solution) dropwise with stirring at -78 C. The resulting solution was stirred for 2 h at -78 C. The reaction was then quenched by the addition of 5 mL of water and diluted with 100 mL DCM. The resulting solution was washed with 50 mL brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column with ethyl acetate/petroleum ether (1:10) eluent, yielding 3-chloro-2-iodo-6-(trifluoromethyl)pyridine as a yellow solid.

According to the analysis of related databases, 823221-95-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Xuqing; Sui, Zhihua; Lanter, James C.; US2011/306592; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-95-0, 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. 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3IN, 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.

Step D 3-chloro-2-iodo-6-(trifluoromethyl)pyridine Into a 100 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-chloro-4-iodo-2-(trifluoromethyl)pyridine (as prepared in the previous step, 2 g, 6.51 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of LDA (730 mg, 6.82 mmol, 1.05 equiv, as a THF solution) dropwise with stirring at -78 C. The resulting solution was stirred for 2 h at -78 C. The reaction was then quenched by the addition of 5 mL of water and diluted with 100 mL DCM. The resulting solution was washed with 50 mL brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column with ethyl acetate/petroleum ether (1:10) eluent, yielding 3-chloro-2-iodo-6-(trifluoromethyl)pyridine as a yellow solid.

According to the analysis of related databases, 823221-95-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Xuqing; Sui, Zhihua; Lanter, James C.; US2011/306592; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 847406-13-7 ,Some common heterocyclic compound, 847406-13-7, molecular formula is C13H17BrN2O2, 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 stirred solution of 7A (0.800 g, 2.55 mmol) in 10 mL toluene was added 2, 3-dichlorophenyl boronic acid (0.975 g, 5.11 mmol) and cesium car- bonate (1. 33 g, 5.62 mmol). The mixture was de- gassed with nitrogen for 10 MIN, THEN E>D (PPh3) 4 (0. 148 g, 0. 128 mmol) was added. The mixture was heated to 85C for 18 h then cooled to ambient tem- perature. The crude product was partitioned between toluene and brine. The organic layer was washed (2 X 30 ML) with brine and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel eluting with 2: 1 EtOAc/Hexane to pro- vide the title compound (0.295 g, 30. 5%) as a light oil which solidified upon standing to a white solid. 1H NMR (CDC13 400 MHz) 5 8.33 (d, J=2. 73 Hz, 1H), 8. 1 (d, J=1.56 Hz, 1H)., 7.51 (dd, J=1.95, 7.80 Hz, 1H), 7.27 (t, J=3.9 Hz, 1H), 7.23 (m, 2H), 4.2 (q, J=7. 02,14. 04 Hz, 2H), 3.71 (m, 2H), 2.91 (m, 2H), 2.49 (m, 1H), 2.05 (m, 2H), 1.9 (m, 2H), 1.28 (t, J=7.41 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847406-13-7, its application will become more common.

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

Electric Literature of 847406-13-7 ,Some common heterocyclic compound, 847406-13-7, molecular formula is C13H17BrN2O2, 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 stirred solution of 7A (0.800 g, 2.55 mmol) in 10 mL toluene was added 2, 3-dichlorophenyl boronic acid (0.975 g, 5.11 mmol) and cesium car- bonate (1. 33 g, 5.62 mmol). The mixture was de- gassed with nitrogen for 10 MIN, THEN E>D (PPh3) 4 (0. 148 g, 0. 128 mmol) was added. The mixture was heated to 85C for 18 h then cooled to ambient tem- perature. The crude product was partitioned between toluene and brine. The organic layer was washed (2 X 30 ML) with brine and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel eluting with 2: 1 EtOAc/Hexane to pro- vide the title compound (0.295 g, 30. 5%) as a light oil which solidified upon standing to a white solid. 1H NMR (CDC13 400 MHz) 5 8.33 (d, J=2. 73 Hz, 1H), 8. 1 (d, J=1.56 Hz, 1H)., 7.51 (dd, J=1.95, 7.80 Hz, 1H), 7.27 (t, J=3.9 Hz, 1H), 7.23 (m, 2H), 4.2 (q, J=7. 02,14. 04 Hz, 2H), 3.71 (m, 2H), 2.91 (m, 2H), 2.49 (m, 1H), 2.05 (m, 2H), 1.9 (m, 2H), 1.28 (t, J=7.41 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847406-13-7, its application will become more common.

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

Electric Literature of 153747-97-8 ,Some common heterocyclic compound, 153747-97-8, 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.

tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (800 mg) was dissolved in DMF (4 ml), and ethyl acrylate (368 mg), palladium(II) acetate (27 mg), tris(2-methylphenyl)phosphine (290 mg), and DIPEA (1.26 g) were added thereto, followed by stirring at 100 C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and then EtOAc was added thereto. The insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl 4-{5-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]pyridin-2-yl}piperazine-1-carboxylate (790 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; US2012/184520; (2012); A1;,
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