Tag: M.W:200-300

Reference of 1235865-75-4, 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. 1235865-75-4, name is Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate. A new synthetic method of this compound is introduced below.

In 100mL2-Boc-octahydropyrrolyl [3,4-c] pyrrole (0.73 g, 3.4 mmol), 2-((1H-pyrrolo [2,3-b] pyridin-5-yl) oxy) -4-fluorobenzoic acidMethyl ester (1.00 g, 3.8 mmol), dipotassium hydrogen phosphate(2.28 g, 10 mmol) and 40 mL of DMSO were reacted at 130 C. for 6 h, cooled to room temperature, 50 mL of water and 30 mLEA, the layers were separated, the aqueous layer was extracted twice with 50 mL of EA, the combined organic phases were washed once with 50 mL of saturated brine,Dried over sodium sulfate, filtered and spin-dried to give 0.702 g of product in 43% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1235865-75-4, Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79456-34-1, 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. 79456-34-1, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4BrF3N2, 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 4) 3-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine; A mixture of the above 5-bromo-3-trifluoromethyl-pyridin-2-ylamine (9.90 g, 41.1 mmol), commercially available 4-(trifluoromethyl)benzeneboronic acid CAS-No. [128796-39-4] (8.58 g, 45.2 mmol), 1N aqueous Na2CO3-solution (98.6 mL, 98.6 mmol) and Pd(PPh3)4 (475 mg, 1 mol %) in DME (205 mL) was refluxed under argon atmosphere for 1 h. Poured into 5% citric acid, extracted with EtOAc, washed the organic layers with sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left a grey solid (13.96 g) which was purified by silica gel flash chromatography with heptane/EtOAc 4:1 to 2:1 to give the title compound as a light yellow solid (10.90 g, 87%). MS (ISN) 305 [(M-H)-]; mp 168 C.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 79456-34-1, 5-Bromo-3-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-30-3, 3-Bromo-5-nitropyridine, 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, 15862-30-3, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-nitropyridine

Preparation of Compound 68B: (0490) To a 25 mL flask was added (E)-tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate (200 mg, 706 mumol), 3-bromo-5-nitropyridine (143 mg, 706 mumol), K2CO3 (293 mg, 2.12 mmol), dimethyl ether (4 mL), water (0.5 mL) and Pd(Ph3P)4 (81.6 mg, 70.6 mumol). Then the mixture was degassed for five times and was heated to 85 C. (oil bath) for 23 hours. The mixture was diluted with EA and water, filtered through celite. The organic layer was separated and the aqueous layer was extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give a brown oil. After purification via combifalsh (eluted with EA/PE=035%), about 160 mg (E)-tert-butyl (3-(5-nitropyridin-3-yl)allyl)carbamate (Compound 68B) was obtained as yellow sticky solid. MS: calc’d 280 (M+H)+, measured 280 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15862-30-3, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; Hoves, Sabine; Wang, Lisha; Yun, Hongying; Zhang, Weixing; Zhu, Wei; (58 pag.)US2016/257653; (2016); 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.135795-46-9, name is 3-Amino-2-bromo-6-methoxypyridine, molecular formula is C6H7BrN2O, molecular weight is 203.04, as common compound, the synthetic route is as follows.Safety of 3-Amino-2-bromo-6-methoxypyridine

2-Bromo-6-methoxypyridin-3-amine (315.6g, 1.56mol, 1.00wt) was charged to a 20000mL flask under nitrogen followed by tetrahydrofuran (2000mL, 6.3vol) and the reaction mixture cooled to -5oC. Sodium bis(trimetylsilylamide) (1M solution in tetrahydrofuran, 3400mL, 3.42mol, 10.9vol) was added dropwise over 2 hours maintaining the temperature below 5oC. The reaction was warmed to room temperature and stirred for 1 hour. The mixture was re-cooled to 0-5oC and di-tert butyl dicarbonate (372.4g, 1.72mol, 1.18wt) solution in tetrahydrofuran (1600mL) added dropwise over 1 hour. The reaction was left to stir under nitrogen over 16 hours after which the 1H-NMR showed complete reaction. Ethanol (6000mL, 19vol) was added to quench the reaction mixture, stirred for 1 hour and concentrated. Dichloromethane (18000mL, 57vol) and saturated ammonium chloride (3000mL, 9.5vol) were charged to the reaction vessel and stirred for 15 minutes. The layers separated and the aqueous layer extracted with dichloromethane (3x 2000mL, 6.3vol). The combined organic fractions were washed with saturated brine (4000mL, 12.7vol), dried over magnesium sulphate, (315g, 1wt), filtered and concentrated under to give a dark red solid (551.4g).The crude product was purified by dry flash chromatography on silica (2x 2200kg, 8wt) eluting with ethyl acetate:heptanes (1:19; Rf 0.28) collecting 2000mL fractions (TLC visualised at UV 254nm and developed by KMNO4). The product containing fractions were combined and concentrated under reduced pressure to give the title compound 19 (368.6g, 78.2%) as a red solid.1H NMR (400MHz, DMSO): d 1.57 (s, 9H), 3.94 (s, 3H), 6.97 (d, J=8.1Hz, 1H), 7.71 (d, J=8.1Hz, 1H), 8.71 (br s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135795-46-9, 3-Amino-2-bromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Article; Badland, Matthew; Devillers, Ingrid; Durand, Corinne; Fasquelle, Veronique; Gaudillire, Bernard; Jacobelli, Henry; Manage, Ajith C.; Pevet, Isabelle; Puaud, Jocelyne; Shorter, Anthony J.; Wrigglesworth, Roger; Tetrahedron Letters; vol. 52; 41; (2011); p. 5292 – 5296;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14529-54-5, Adding some certain compound to certain chemical reactions, such as: 14529-54-5, name is 3,5-Dibromo-1-methylpyridin-2(1H)-one,molecular formula is C6H5Br2NO, 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 14529-54-5.

Example 304c 5-Bromo-3-(5-(2-methoxyethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-1-methylpyridin-2(1H)-one 304c A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 304b (230 mg, 1.17 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (468.4 mg, 1.76 mmol), Pd2(dba)3 (53.5 mg, 0.0585 mmol), Xantphos (67.6 mg, 0.117 mmol), Cs2CO3 (762.8 mg, 2.34 mmol), and dioxane (20 mL). After three cycles of vacuum/N2 flush, the mixture was heated at 100C for 3 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. It was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 304c as a dark solid (380 mg, 85%). MS-ESI: [M+H]+ 382.2

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. 14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1222185-12-7, 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 1222185-12-7 as follows.

(E)-Dimethyl 3-styrylpyridine-2,4-dicarboxylate Z4’A stirred suspension of 3-bromopyridine 11 (500 mg, 1.82 mmol, 1 eq.), (E)-styryl boronic acid (300 mg, 2.01 mmol, 1.1 eq.), Cs2CO3 (650 mg, 2.01 mmol, 1.1 eq.), Pd(OAc)2 (40 mg,0.182 mmol, 0.1 eq.) and PPh3 (100 mg, 0.365 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 0C for 5 h in an oil bath. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo.The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EpsilontOAc/hexane) to afford Z4′ (322 mg, 60%) as an off-white solid.1U NMR deltaH (400 MHz; CDCl3) 3.86 (s, 3H, OCH3), 3.89 (s, 3Eta, OCH3), 6.59 (d, J=16.5 Hz, IH, CH=CH), 7.23-7.30 (t, J=8.0 Hz, IH, ArHpara), 7.34 (t, J=8.0 Hz, 2H, ArHmeta), 7.46 (d, J=7.0 Hz, 2H, ArHortho), 7.64 (d, J=16.5 Hz, IH, CH=CH), 7.71 (d, J=5.0 Hz, IH, pyHmeta), 8.65 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.8 (CH3), 52.8 (CH3), 123.5 (CH=CH), 124.6 (ArCH), 126.7 (ArCH), 128.4 (ArCH), 128.7 (ArCH), 133.0 (ArQ, 135.1 (CH=CH), 136.5 (ArQ, 139.0 (ArQ, 147.9 (ArCH), 149.8 (ArQ, 166.5 (CO), 166.7 (CO); IR vmax (filmycrn 1 2953, 1735, 1447, 1434, 1313, 1269, 1197, 1166, 1143, 1130; HRMS (EpsilonSI+) for C17H15NNaO4 requires 320.0893, found (M+Na*) 320.0893;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1222185-12-7, its application will become more common.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1207557-35-4 ,Some common heterocyclic compound, 1207557-35-4, molecular formula is C11H11BrN2O3, 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.

Step B: DecarboxylationA solution of ethyl 6-bromo-4-methoxylpyrazolo[l,5-a]pyridine-3-carboxylate (15, 5.2 g, 18.24 mmol) in HBr (100 ml, 884 mmol) was heated to 100 0C for 1 hour. After cooling to 0 0C, IM NaOH (182 ml, 912 mmol) was used to neutralize the solution. The reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydroxide (IN) and brine then dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography (0-35% EtOAc in hexanes, linear gradient) to give 6-bromo-4- methoxypyrazolo[l,5-alpha]rhoyridine (16, 2.475 g, 10.90 mmol, 60 % yield). MS APCI: (M + H]+ m/z 228.1.; Scheme 2.Molecules of type 21 were prepared according to scheme 2. O- Mesitylenesulfonylhydroxylamine (1) was used to access W-imino-pyridinium mesitylenesulphonate 14. [3+2] Cyclization of 2 with ethyl propiolate yields pyrazolopyridine 15. Decarboxylation in neat hydrobromic acid afforded 16. Functional ization of the 6-position of the pyrazolopyridine core is accomplished via a Suzuki coupling reaction to install aryl or heteToaromatic functionality (17) using known or commercially available boronic acids or esters. For specific boronic ester examples, see WO 2004052286 A2 and WO 2007085873 Al . Halogenation via reaction with //-iodosuccinimide enables a second Suzuki coupling of iodide 18 with thiophcnc boronic ester to yield coupling product 19. Hydrolysis of the ester yielded acid 20 and subsequent coupling with an amine yielded target 21.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1207557-35-4, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; KATZ, Jason; KNOWLES, Sandra, L.; JEWELL, James, P.; SLOMAN, David, L.; STANTON, Matthew, G.; NOUCTI, Njamkou; WO2010/17046; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 29682-15-3, 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 29682-15-3 as follows.

This compound is synthesized as described by adaptation of the following reference: Tye et al., Tet. Lett., 2008, 49, 3939. To a stirred suspension of methyl-5-bromo-2- pyridine carboxylate (0.25 g, 1.16 mmol) and 2-(trimethylsilyl)pyridine (0.48 mL), 3.48 mmol) in anhydrous N,N-dimethyl formamide (7.5 mL) is added silver (I) oxide (0.27 g, 1.16 mmol), allyl palladium chloride dimer (21 mg, 5 mol%) and tetrabutyl ammonium fluoride (IM in THF, 0.116 mL). The reaction is heated at 90 0C for 18 h. The reaction mixture is filtered and washed with EtOAc. The filtrate is concentrated under reduced pressure. Purification by column chromatography (silica, eluent DCM, 0- 2% MeOH) gives 0.12g (48%) of methyl 2,3′-bipyridine-6′-carboxylate. m/z = 215 [M++H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29682-15-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COGAN, Derek; MOSS, Neil; SARKO, Christopher Ronald; BAMFORD, Samantha Jayne; LOKE, Pui Leng; NAPIER, Spencer Charles, R.; TYE, Heather; WHITTAKER, Mark; WO2010/80357; (2010); 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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one

To a solution of phosphoryl chloride (2.0 mL, 21.2 mmol) and quinoline (1.30 mL, 10.8 mmol) was added solid powder 3-nitro-5-(trifluoromethyl)pyridin-2-ol (4.00 g, 18.3 mmol) (95% purity). The resulting dark brown thick suspension was heated to reflux for 4 h and gradually turned into a very cloudy dark brown solution. After cooling to 100 C., water (11 mL) was slowly added to the mixture which was further cooled to room temperature and neutralized carefully with Na2CO3. The resulting solution was extracted with EtOAc three times. The extracts were combined, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexanes 30:70) to afford 2.28 g of desired product.

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, 33252-64-1, 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one.

Reference:
Patent; Xue, Chu-Biao; Zheng, Changsheng; Feng, Hao; Xia, Michael; Glenn, Joseph; Cao, Ganfeng.; Metcalf, Brian W.; US2006/4018; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 70201-42-2, Adding some certain compound to certain chemical reactions, such as: 70201-42-2, name is 3,5-Dibromoisonicotinaldehyde,molecular formula is C6H3Br2NO, 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 70201-42-2.

Compound 1-1 (50.0 g, 188.7 mmol) and compound 1-2 (31.0 g, 190.7 mmol) are combined in a flask and treated with NMP (250 mL) and the resulting mixture is stirred for 2 hours. 50% aqueous KOH solution (27.4 g, 415.2 mmol KOH in 27.4 mL water) is then added and the resulting mixture is heated at 80 C for 60 minutes. Water is then added at 80C and the resulting mixture is cooled to ambient temperature over 4-16 hours. The resulting solid is collected by filtration, washed with water and dried to afford compound 1-3 as a solid (51.5 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. 70201-42-2, 3,5-Dibromoisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HUBER, John David; WO2011/137109; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem