Tag: M.W:200-300

Reference of 637348-81-3, Adding some certain compound to certain chemical reactions, such as: 637348-81-3, name is 3-Bromo-5-iodopyridin-2-ol,molecular formula is C5H3BrINO, 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 637348-81-3.

Example 142b 3-Bromo-5-iodo-1-methylpyridin-2(1H)-one 142b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (50 mL), 142a (6.0 g, 20.0 mmol), CH3I (4.26 g, 30.0 mmol), and K2CO3 (5.52 g, 40.0 mmol). The mixture was stirred at room temperature for 2 h and diluted with water (200 mL). The resulting white solid was collected by filtration to afford 142b (5.97 g, 95%) as a white solid. MS-ESI: [M+H]+ 314

According to the analysis of related databases, 637348-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 69045-83-6, 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 69045-83-6 as follows.

2, 3-dichloro-5-trichloromethylpyridine (36.60 g, 0.139 mol) was added to a flask containing acetic acid (53.50 g, 0.892 mol) and methanol (200 mL). The mixture was cooled to-5 C, and zinc dust (20.01 g, 0.308 mol) was added in small portions at 10 minute intervals. The mixture was stirred mechanically for 4 hours, filtered, and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with brine, followed by saturated aqueous sodium bicarbonate, followed by a second brine wash. The organic phase was dried over magnesium sulfate and concentrated in vacuo to yield 21.55 g (79%) of Preparatory Compound P, 2, 3-DICHLORO-5- (CHLOROMETHYL) pyridine, as a yellow liquid (about 65% PURITY). 1H NMR No. 8.31 (d, 1H, J=2.3 Hz), 7.85 (q, 1H, J=0.4 Hz and J=2.2 Hz), 4.56 (s, 2H). MS (ESI) NIZ 199 ([M+4] +, 8), 197 ([M+2]+, 27), 195 ([M]+, 28), 164 (11), 162 (66), 160 (100), 124 (19)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-83-6, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; WO2004/57960; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866775-18-0, Adding some certain compound to certain chemical reactions, such as: 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate,molecular formula is C8H6BrF3N2O2, 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 866775-18-0.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 ml); Sodium hydroxide (2.0 M aqueous solution) (14.04 ml, 28.1 mmol) was added and the suspension was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 ml) and then acidifed by the addition of 5.0M HCI(aq). The product was extracted into ethyl acetate (2 x 75 ml) and the combined organic extracts were washed with water (50 ml), brine (25 ml), dried (MgS04) and concentrated in vacuo to afford the title product as a yellow solid. 1H-NMR: [400MHz, DMSO-de, deltaEta 13.24 (1 H, br s, C02H), 7.74 (1 H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1 , 287.1 [M+H]+

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. 866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58236-70-7, 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 58236-70-7 as follows.

Step2: 5-Bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridine[254][255]Potassium carbonate (2.0 eq.) was added to a solution of tetrahydro-2H-pyran-4-yl methanesulfonate (1.2 eq.) and 5-bromo-3-chloropyridine-1-ol (1.0 eq.) in N,N-dimethylformamide (0.2 M). The reaction mixture was stirred at 100 for 18 h. The reaction mixture was allowed to reach room temperature, diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. The resultant residue was purified by flash column chromatography on silica gel to afford 5-bromo-3-chloro-2-((tetrahydro-2H-pyran-4-yl) oxy) pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58236-70-7, its application will become more common.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; KANG, Jae-Hoon; LEE, Hong-Sub; AN, Kyung-Mi; HONG, Chang-Hee; KWAK, Hyun-Jung; CUI, Shuo-Lin; SONG, Hyo-Jung; (55 pag.)WO2018/111012; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1186637-43-3, 3-Bromo-6-methoxypicolinonitrile, 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 3-Bromo-6-methoxypicolinonitrile, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-6-methoxypicolinonitrile

A solution of 2-(te/i-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methoxypicolinonitrile (from step 1) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol%) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 1000C and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-50% ethyl acetate in hexane to give 3- methoxybenzo[f][l,7]naphthyridin-5-amme as a yellow solid. 1H NMR (acetone J-6): delta 8.91 (d, IH), 8.34 (d, IH), 7.63 (d, IH), 7.51-7.53 (dd, IH), 7.27-7.33 (m, 2H), 6.65 (br, 2H), 4.11 (s, 3H). LRMS [M+H] = 226.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1186637-43-3, 3-Bromo-6-methoxypicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 364793-93-1, 4-((6-Bromopyridin-3-yl)methyl)morpholine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a RB flask containing formylpyridine (9.347 g, 1 equiv.) in 175 mL 1,2-dichloroethane (3.5 mL/mmol) was added morpholine (4.7 mL, 1.07 equiv.) followed by NaBH(OAc)3 (14.819 g, 1.4 equiv.) and acetic acid (3.1 mL, 1.07 equiv.). The flask was loosely capped and the mixture was stirred at r.t. Mixture gets slightly warm. After 40 min, the reaction was quenched with saturated NaHCO3. When the gas evolution was greatly reduced, 1M NaOH was added to bring the pH to 8-9. The two layers were separated and the aqueous layer was extracted with DCM (×3). The organic layer was dried over Na2SO4, filtered and solvent was removed in vacuo. The product was filtered through silica with 1000 mL 100:1 EtOAc:NH4OH to remove baseline material. The material was dissolved in 15 mL EtOAc and 150 mL hexanes was added. The mixture was allowed to sit overnight at 4 C. to crystallize. The supernatant was decanted off and the crystals were washed with a little hexanes which was decanted off. The crystals were transferred to another flask using DCM. LC-MS showed only product. The solvent from the supernatant was removed in vacuo. The remaining mixture was purified by flash column (6.5×8.5 cm silica) using 500 mL 8:2 EtOAc; 1400 mL 100:1 EtOAc:NH4OH. All product fractions were combined giving 10.931 g (85%) of the 4-((6-bromopyridin-3-yl)methyl)morpholine as a yellow solid.In a RB flask, a mixture of 4-((6-bromopyridin-3-yl)methyl)morpholine (10.959 g, 1 equiv.), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (10.478 g, 1.05 equiv.), 2M potassium phosphate solution (42.5 mL, 2 equiv.) and Pd(PPh3)4 (2.479, 0.050 equiv.)) in 210 mL dioxane (5 mL/mmol) was sparged with argon for 5 min. The flask was fitted with a septum and argon balloon and the mixture was stirred at 100 C. (amber solution). After 27 h, the mixture was allowed to cool then volume was reduced by at least half in vacuo. The remainder was diluted with water and extracted with EtOAc (×3). The organic layers were washed with brine, dried over Na2SO4, filtered and solvent was removed in vacuo. The material was purified by column chromatography on silica eluting with DCM:MeOH to give 10.268 g (85%) of 4-methyl-3-(5-(morpholinomethyl)pyridin-2-yl)aniline as a very viscous dark amber oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,364793-93-1, 4-((6-Bromopyridin-3-yl)methyl)morpholine, and friends who are interested can also refer to it.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 179687-79-7, 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.179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, molecular formula is C12H9ClN2O3, molecular weight is 264.66, as common compound, the synthetic route is as follows.

2-chloro-4-nitro phenol 1Og (57.6 mmol, leq), 2-pycolyl chloride hydrogen chloride 9.45g (57.6 mmol, 1 equiv) cesium carbonate 41.3 (126.8 mmol, 2.2 equiv) and sodium iodide 8.64g (57.6 mmol, 1 equiv) were suspended in 200 mL acetonitrile. The reaction mixture was stirred at 60C for 5h. The resulted suspension was filtered and washed with 400 mL water, yielding 2-(2-chloro-4-nitro-phenoxymethyl)-pyridine (8g, 52%) as a red solid. 2-(2-chloro-4-nitro-phenoxymethyl)-pyridine (8 g, 30.2mmol, 1 equiv) and 8.44g iron (151.1 mmol, 5 equiv) were mixed in 100 mL acetic acid and 50 mL EtOAc and were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The solution was extracted with EtOAc and the organic layer was washed with brine and concentrated in vacuo. The resulting crude material was purified by flash chromatography eluting with EtOAc/hexane (3:7) to give 3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine (3.2 g, 52%) as a white solid. 1H-NMR (CDCl3) delta 5.18 (s, 2H), 6.50 (dd, IH), 6.76 (d, IH),. 6.80 (d, IH), 7.22 (m, IH), 7.64 (d, IH), 7.73 (td, IH), 8.55 (m, IH); LCMS RT = 0.89 min; [M+H]+ = 235.1.

Statistics shows that 179687-79-7 is playing an increasingly important role. we look forward to future research findings about 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; ZHANG, Chengzhi; WO2006/23843; (2006); A2;,
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. 1256811-02-5, name is 1-(5-Bromo-2-methoxypyridin-3-yl)ethanone, molecular formula is C8H8BrNO2, 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. Recommanded Product: 1256811-02-5

To a solution of l-(5-bromo-2-methoxypyridin-3-yl)ethanone (2.0 g, 8.69 mmol) in HBr (20 mL, HO Ac solution), Br2 (1.4 g, 8.76 mmol) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. Then the reaction mixture was filtered to collect the HBr salt. The solid was suspended with Na2C03 solution, extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to provide 2-bromo-l-(5-bromo-2- hydroxypyridin-3-yl)ethanone (2.0 g, yield: 74%). 1H- MR (DMSO, 400 MHz) delta 12.83 (br s, 1H), 8.11-8.13 (m, 2H), 4.85 (s, 2H). MS (M+H)+: 295.

With the rapid development of chemical substances, we look forward to future research findings about 1256811-02-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; HE, Shuwen; DAI, Xing; LIU, Hong; LAI, Zhong; LONDON, Clare; XIAO, Dong; ZORN, Nicolas; NARGUND, Ravi; WO2013/33971; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, 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 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-3-(difluoromethoxy)pyridin-2-amine

To a mixture of 5-bromo-3-(difluoromethoxy)pyridin-2-amine (1.00 g, 4.18 mmol) in EtOH (10.0 mL) was added 2-bromo-l, l-di ethoxy ethane (1.07 g, 5.44 mmol, 818 uL) and HBr (7.45 g, 30.4 mmol, 5.00 mL, 33% in HOAc), and the mixture was stirred at 90 C for 16 h. The mixture was concentrated under reduced pressure to remove EtOH, and the residue was dissolved into ethyl acetate (50.0 mL) and washed with NaHC03 (50 mL) and brine (50.0 mL). The organic layer was dried with Na2S04, then concentrated under reduced pressure to give 6-bromo-8-(difluorom ethoxy )imidazo[l,2-a]pyri dine (900 mg, 3.42 mmol, 82% yield) as a brown solid. LC-MS (ESI+) m/z 265.1 (M+H)+; 1HNMR (400 MHz, MeOD): d 8.67 (s, 1 H), 7.98 (d, 1 H), 7.67 (s, 1 H), 7.29 (s, 1 H), 7.46 – 7.10 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, and friends who are interested can also refer to it.

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

Electric Literature of 1190862-70-4, Adding some certain compound to certain chemical reactions, such as: 1190862-70-4, name is Ethyl 5-bromo-6-methylnicotinate,molecular formula is C9H10BrNO2, 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 1190862-70-4.

16A: Ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate : A degassed solution of ethyl 5-bromo-6-methylnicotinate (600 nig, 2.458 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (874 mg, 3.44 mmol), potassium acetate (374 mg, 3.81 mmol) and PdCl2(dppf)-CH2Cl2 adduct (161 mg, 0.197 mmol) in dioxane (10 mL) was heated to 60 C with vigorous mixing ON. The reaction mixture was concentrated onto Celite, then purified by flash chomatography utilizing a 40g ISCO column and eluting with 0-90% EtOAc in hexanes. The pure fractions were concentrated to afford ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (490 mg, 1.599 mmol, 65.0 % yield) as a waxy white solid. MSESI m/z 291.8 (M+H)

According to the analysis of related databases, 1190862-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MERTZMAN, Michael E.; DZIERBA, Carolyn Diane; GUERNON, Jason M.; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; SPERGEL, Steven H.; (245 pag.)WO2019/89442; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem