Month: April 2022

Synthetic Route of 866546-09-0, Adding some certain compound to certain chemical reactions, such as: 866546-09-0, name is 3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H4BrClN2, 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 866546-09-0.

[0231] Step 2: l-(Benzenesulfonyl)-3-bromo-5-chloro-pyrrolo[2,3-b]pyridine. NaH (60% dispersion in oil, 0.33 g, 8.3 mmol) was added to a solution of 3-bromo-5-chloro-lH- pyrrolo[2,3-b]pyridine (1.28 g, 5.5 mmol) in DMF (25 mL) at room temperature. The reaction was stirred for 10 min. and then /?-toluenesulfonyl chloride (1.06 mL, 8.3 mmol) was added and the reaction stirred for an additional 2 h. Water (50 mL) was added, the mixture extracted with EtOAc (3 x 50 mL), the organic layers combined, dried over sodium sulfate, filtered and evaporated to dryness. Purification by column chromatography (hex/EtOAc) and recrystallization from hex/EtOAc afforded the desired product (1.45 g, 70%). 1H NMR (400 MHz, DMSO- e) delta ppm 8.50 (d, 1 H), 8.35 (s, 1 H), 8.13 (dd, 1H), 8.12 (d, 2H), 7.76 (dt, 1 H), 7.65 (t, 2 H).

According to the analysis of related databases, 866546-09-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALZHEIMER’S INSTITUTE OF AMERICA, INC.; SEBAHAR, Paul R.; HALTER, Robert J.; MCLEOD, Donald A.; PARKER, Daniel P.; YAGER, Kraig M.; SHENDEROVICH, Mark D.; HOLCOMB, Ryan C.; RICHARDS, Burt; BARTEL, Paul L.; KIM, Se-Ho; SLATTUM, Paul M.; TANGALLAPALLY, Rajendra; TROVATO, Richard; YUNGAI, Ashantai J.; WO2014/4863; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1 ,Some common heterocyclic compound, 1206978-11-1, molecular formula is C6H3BrF3NO, 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.

3-Trifluoromethoxy picolinic acid (24); At -100 0C, butyllithium (1.56 M in hexane, 5.5 mL, 8.3 mmol, 1 eq) was added dropwise to a solution 2-bromo-3-trifluoromethoxy pyridine (23, 2.0 g, 8.3 mmol) in dried toluene (15 mL). After 2 h at -78 0C, the mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6N, 4 mL) before being extracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford pure 3-trifluoromethoxy picolinic acid (24, 1.1 g, 5.3 mmol, 64%) as a white powder; m.p. 84-87 0C.1H NMR (CD3OD, 300 MHz): delta = 8.54 (d, J= 4.5 Hz, 1 H), 7.87 (d, J = 8.5 Hz, 1 H), 7.63 (dd, J= 8.5, 4.5 Hz, 1 H). – 19F NMR ((CD3)2CO, 282 MHz): delta = -58.7 – 13C NMR(CD3OD, 75 MHz): delta = 164.5, 147.5, 144.5, 143.4, 131.2, 127.6, 120.3 (q, J= 260 Hz).- C7H4F3NO3 (207): calcd. (%) C 40.59, H 1.95, N 6.76; found C 40.21, H 2.17, N 6.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206978-11-1, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3279-76-3, 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.3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.

1) 3-Bromo-2-methoxy-5,8-dimethyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine A mixture of 2-hydroxy-6-methylpyridine (164 g, 1.47 mol), iodomethane (1.35 kg, 9.53 mol), Ag2CO3 (526 g, 1.91 mol) in THF (10 ml) was strirred overnight at ambient temperature while protecting from light. The mixture was filtered through Celite and the filter cake was washed with THF. The filtrate was concentrated in vacuo until all methyl iodide was removed by HPLC analysis to yield 145.6 g (80%) of 2-methoxy-6-methylpyridine.

The chemical industry reduces the impact on the environment during synthesis 3279-76-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Forest Laboratories Holdings Limited; US2007/281918; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde. A new synthetic method of this compound is introduced below.

n-Butyllithium (2.063ml, 5.16 mmol) was added to -40 C solution of 1 -bromo-4-(trifluoromethyl)benzene (0.722 ml, 5.16 mmol) in THF (30 ml) and this solution was stirred at -40 C for 1 h. A solution of 5-chloronicotinaldehyde (730 mg, 5.16 mmol) in THF (5 mL) was added and the solution was stirred at -40 C for 1 h and then at 0 C for 1 h. The reaction was then quenched with saturated aqueous NH4C1 solution. The product was extracted with ethyl acetate. The organic extract was dried over Na2504, filtered, and concentrated. No further purification is necessary. ?H NMR (500 MHz, CDC13) oe: 8.54 (s, 1H), 8.48 (s, 1H), 7.78 (s, 1H), 7.66 (d, J= 8 Hz, 2H), 7.53 (d, J= 8 Hz, 2H), 5.97(s, 1H), 3.55 (broad s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; WILSON, Jonathan, E.; MCCRACKEN, Troy; (95 pag.)WO2016/179059; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53554-20-4, Adding some certain compound to certain chemical reactions, such as: 53554-20-4, name is 6-Amino-2-chloronicotinonitrile,molecular formula is C6H4ClN3, 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 53554-20-4.

To a 40 mL pressure vial were added 6-amino-2-chloronicotinonitrile (1.000 g, (0806) 6.51 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (1.423 g, 8.47 mmol), K2CO3 (1.350 g, 9.77 mmol), followed by 1,2-dimethoxy ethane (16 mL), water (8 mL) and then Pd(PPh3)4 (0.226 g, 0.195 mmol). Argon was bubbled through the mixture. The reaction mixture was heated at 80 C overnight in a heating block. The reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with brine. (0807) The organic layer was separated and concentrated. The material was purified using silica gel chromatography eluting with 0-80% B/DCM over 13 minutes. [B= 10% 2 N NH3 in MeOH/EtOAc]. The appropriate fractions were concentrated to afford 6-amino-2-(prop- l-en-2-yl)nicotinonitrile (0.878 g, 5.52 mmol, 85% yield), as an off-white solid. NMR (400 MHz, DMSO-de) delta 7.70 (d, J=8.8 Hz, IH), 7.01 (br. s., 2H), 6.42 (d, J=8.8 Hz, IH), 5.49-5.43 (m, 2H), 2.07 (t, J=l. l Hz, 3H).

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. 53554-20-4, 6-Amino-2-chloronicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ARAUJO, Erika M. V.; CHEN, Yan; DASGUPTA, Bireshwar; DEGNAN, Andrew P.; HILL, Matthew D.; KUMI, Godwin Kwame; MASTALERZ, Harold A.; WITTMAN, Mark D.; PEARCE, Bradley C.; ZHANG, Guifen; (172 pag.)WO2019/90198; (2019); 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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 6-Chloro-5-nitronicotinic acid

a. To a solution of 6-chloro-5-nitronicotinic acid in acetic acid (240 ml) was added iron (20 g) and the mixture was heated with stirring on a steam bath. After 11/2 hours, the mixture was filtered hot and washed with hot acetic acid. The filtrate was concentrated to dryness and the residue was treated with 10% NaOH, filtered and the pH adjusted to 2-3. The solid was filtered to yield 8.0 g (60% yield) of 5-amino-6-chloronicotinic acid.

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4279913; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8 , The common heterocyclic compound, 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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.

N-({[(fra/?s-4-{[(methylethyl)sulfonyl]amino}cyclohexyl)methyl]amino}thioxomethyl) amide (0.60 g, 2.0 mmol) was added to a stirred solution of 2-bromo-1-(2- pyridyl)ethan-1-one hydrobromide (0.57 g, 2.0 mmol) in EtOH (20 ml_) at rt followed by the addition of DIEA (1.05 ml_, 6.0 mmol). The reaction mixture was heated at reflux for 4 h, cooled to rt, and concentrated in vacuo. The resultant residue was re- dissolved in CHCI3 and washed successively with aqueous citric acid, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (60 % EtOAc in Hexanes) to afford the desired product as a tan colored solid (0.56 g, 69 %). 1H NMR (CDCI3) delta 8.58 (d, 1 H, J=4.8 Hz), 7.89 (dt, 1 H, J=7.6 and 1.2 Hz), 7.71 (td, 1 H, J=7.8 and 2.0 Hz), 7.17 (td. 1 H, J=4.8 and 1.2Hz), 5.25 (br s, 1 H), 3.85 (d, 1 H1 J=8.4 Hz), 3.25 (br m, 1 H), 3.18 (t, 2H, J=6.4 Hz), 2.14 (dt, 2H, J=12.0 and 1.2 Hz), 2.19 (br, d, EPO 2H, J=12.8 Hz), 1.62 (br m, 3H), 1.38 (d, 6H, J=6.8 Hz), 1.25 (dq, 2H, J=12.8 and 1.6 Hz). LC-MS m/e: 395 (M+H)+; tR = 2.14 min (Method-A).

The synthetic route of 17570-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2007/2126; (2007); A1;,
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. 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine, molecular formula is C6H4BrClN2O2, 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. SDS of cas: 186413-75-2

To a stirred solution of 3-bromo-6-chloro-2-methyl-5-nitropyridine (2.00 g, 7.95 mmol) in tetrahydrofuran (16 mL) at -78 C. was added (E)-but-2-en-2-ylmagnesium bromide (0.5M in THF) (55.7 mL, 27.8 mmol). The reaction mixture was allowed to warm to ?35 C. over 30 min. and was then quenched with a saturated aqueous solution of ammonium chloride. The mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, washed with brine, and dried over anhydrous sodium sulfate. The organic layer was collected, and the aqueous layers were sequentially washed extracted with ethyl acetate (2*). The combined organic layers were dried over anhydrous sodium sulfate, and the resulting residue was purified by ISCO flash silica gel chromatography (24 g column; gradient: 0%-100 ethyl acetate in hexane) to give 4-bromo-7-chloro-2,3,5-trimethyl-1H-pyaolo[2,3-c]pyridine (0.402 g, 1.47 mmol, 19% yield) as a yellow solid. The product had a UPLC ret. time=1.14 min. -Column: PHENOMENEX Kinetex C18 2.1×50 mm (1.5 min. gradient); Solvent A=10% MeCN, 90% H2O, 0.1% TFA; Solvent B=90% MeCN, 10% H2O, 0.1% TFA. LC/MS M+1=273.2 and 275.2.

With the rapid development of chemical substances, we look forward to future research findings about 186413-75-2.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-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, Computed Properties of C6H5BrN2O, blongs to pyridine-derivatives compound. Computed Properties of C6H5BrN2O

EXAMPLE 251 : 5-(6-(trifluoromethyl)- lH-indazol-4-yl)picolinamide [0794] A vial was charged with a mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)-6-(trifluoromethyl)-lH-indazole (0.05 g, 0.160 mmol), 5-bromopicolinamide (0.042 g, 0.208 mmol) and PdCl2(dppf) (5.86 mg, 8.01 muiotaetaomicron) in dioxane (8 mL) and aqueous saturated NaHC03 (2 mL). The resulting light brown suspension was heated at 140C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 25-45% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA) over a period of 6 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as an off white solid (19 mg, 0.062 mmol, 39%). 1H NMR (400 MHz, DMSO-<) delta ppm 7.66 (s, 1 H), 7.77 (br s, 1 H), 8.06 (s, 1 H), 8.14-8.33 (m, 1 H), 8.37-8.49 (m, 1 H), 9.00-9.08 (m, 1 H), 13.84 (br s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci4H9F3N40, 307.1; found 307.15. The synthetic route of 90145-48-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); 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. 582303-10-4, name is (2,6-Dimethylpyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 582303-10-4

Step B: 3-(chloromemviy2,6-dimethylpyridine (3)The solution of compound (2,6-dimethylpyridin-3-yl)methanol (0.76 g, 5.6 mmol) in SOCl2(5 mL) was stirred at room temperature for 1 hour and then concentrated to give the crude product 3 which was used for next step directly without further purification. LCMS (ESI) m/z = 156.1 (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, 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; MCCOMAS, Casey, C.; REGER, Thoma, S.; QI, Changhe; WO2014/150114; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem