Tag: M.W:200-300

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.6945-67-1, name is 2-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.Product Details of 6945-67-1

The 2-[1-hydroxy-1-[4-(naphth-2-ylmethoxy)pyrid-2-yl]propyl]thiazole used as a starting material was obtained as follows: 2-Naphthylmethanol was reacted with 2-bromo-4-nitropyridine (Chem. Abstracts, 1951, 45, 9536) using the conditions described in the first paragraph of the portion of Example 4 which is concerned with the preparation of starting materials except that the reaction mixture was stirred at ambient temperature for 2 hours. There was thus obtained 2-bromo-4-(naphth-2-ylmethoxy)pyridine in 80% yield, m.p. 99-100 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6945-67-1, 2-Bromo-4-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; ICI Pharma; Imperial Chemical Industries PLC; US5089513; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 717843-56-6, 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 717843-56-6 as follows.

To 3-bromo-2-methoxy-5-methylpyridine [CAS 717843-56-6] (1.0 g, 4.95 mmol) in 20 mL of dry tetrahydrofuran was added Q-Phos (1,2,3,4,5-pentaphenyl-1?-(di-tert-butylphosphino)ferrocene) (0.077 g, 0.109 mmol) and bis(dibenzylideneacetone)palladium (0.091 g, 0.099 mmol). A solution of freshly-prepared (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (2.419 g, 9.90 mmol) in tetrahydrofuran (0.45 mmol/mL, 17 mL) was added via a stainless steel cannula under nitrogen pressure. The mixture was stirred at ambient temperature for 40 minutes. Dichloromethane and saturated aqueous NH4Cl were added. The organic layer was washed with brine and concentrated. The residue was purified via chromatography on a 40 g silica gel cartridge, eluting with ethyl acetate in 48 heptane at 0-50% gradient to yield 136 methyl 1-(2-methoxy-5-methylpyridin-3-yl)cyclopropanecarboxylate which was dissolved in 28 methanol (10 mL) and 6M 137 aqueous lithium hydroxide (3 mL) and stirred at 50 C. for 15 hours. The solvent was removed, and 25 water (10 mL) was added. The aqueous layer was extracted with ethyl acetate (10 mL×2). The aqueous layer was adjusted pH 1-2 and extracted with dichloromethane (30 mL×3), and the extracts washed with brine, dried over MgSO4 and concentrated to provide the 138 title compound which used in next step without further purification. MS (APCI+) m/z 208 (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,717843-56-6, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 3430-26-0, name is 2,5-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below., Product Details of 3430-26-0

Intermediate 43. Step 1; 5-bromo-4-methylpicolinic acid To a solution of 2,5-dibromo-4-methylpyridine (3 g, 11.96 mmol) in anhydrous toluene (40 ml)) was added BuLi (5.74 ml, 14.35 mmol) at -78 °C dropwise. The reaction mixture was stirred at – 78 °C for 1 h. Then the reaction mixture was poured into a 100 mL beaker with dry carbon dioxide (4 g, 91 mmol). The reaction mixture was stirred at 20 °C for another 10 minutes. Then the mixture was poured into saturated citric acid and a yellow precipitate was formed. The suspension was filtered and the solid was collected, dried in vacuo to give 5-bromo-4- methylpicolinic acid. 1HNMR (400 MHz, DMSO-i): delta = 8.71 (s, 1 H), 7.99 (s, 1 H), 2.40 (s, 3 H). MS: 215.9 (M+l) ppm.

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, 3430-26-0, 2,5-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; XU, Jiayi; YU, Wensheng; YU, Younong; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (211 pag.)WO2016/109221; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 26163-03-1, 3-Bromo-5-chloropyridin-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, 26163-03-1, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Bromo-5-chloropyridin-2-amine

a sobthDn of 2-amiao-Thlznio-&cIueolopydin? (10.0 g, 4S.2 mmol7 Ark Phmm iii Nfl dim?thyl.fcamumide (2] niL) was ailed DMF-DMA (17.2 g, 145 nutol) anl the nthrthre was sbned13] C fca abc?at 18 K The mixbare was cooled aat evapcnted to thyness. To an ice cooled Hn sob fioiiofthebrcwiisolid iiiMeOH (JO mL) ardpyridim (7.8QniL, %nutiol)was added hthor,r1anthie-o-sulforth td (73g, 675 nmnol). TIE rac&iwas allowed to wanr to thciat 25anl stind fbr about 13 K The nuethr? was evapra±ed and the solid iesithie was dissohd in DCM (150 mL) aid washel with ;aturated o1±uaubicaabointe (10 niL), water (20] niL) ard biine (10 nL). The oigai& nuethre was filtered though a Eiote phase sepantc to renrn iesi&ial wateraiid evapcnted to thyrs to give ?-Ch1 [LZ4]1rio1o[L5-a]pth2e as an cnie soli4 whck was used iii th n?xttep witlout fint1r purificaiiou.. (.l g, 64% nude): ?H NMR (CDC1.)i5 2155(d, 1 1.3Hz, 1H), 239 (s, 1H), 7SJ (, 1 1.7Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26163-03-1, its application will become more common.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FRIEDMAN, Michael M.; COX, Philip; FRANK, Kristine E.; HOEMANN, Michael Z.; OSUMA, Augustine; WILSON, Noel S.; XU, Xiangdong; WO2015/157955; (2015); 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. 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-2-iodopyridin-3-amine

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%). To a mixture containing 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) and Intermediate 5A-2 (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (111 mg, 0.36 mmol), and Pd(dppf)C12 (10.5 mg, 0.014 mmol) in a screw cap vial was added THF (2.5 mL) followed by 3M aqueous solution of tripotassium phosphate (0.10 mL, 0.3 mmol). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 75 C. for 3 h. The reaction mixture was cooled to room temperature and treated with saturated aqueous NaCl solution (5 mL) and extracted with ethyl acetate (3*10 mL). The extracts were combined, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified on silica gel column chromatography eluting with a 10 min gradient from 5%-100% DCM/EtOAc. No separation was observed. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate was isolated (100 mg, 77% yield), m/z (550, M+1) and was used as such in subsequent step. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (95 mg, 0.21 mmol) was dissolved in MeOH (5 mL) and transferred to a Parr bottle. The mixture was purged with nitrogen. Pearlman’s Catalyst (25 mg, 0.036 mmol) was added and the bottle was pressurized with hydrogen gas (50 psi) and shaken for 22 h. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated. The resulting residue was dissolved in a small amount of DCM and charged to a silica gel column, which was eluted over a 10 min gradient with 1%-5% MeOH/DCM to afford a mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5C) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (82 mg, 80%), m/z (452, M+H).

The synthetic route of 915006-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 132521-70-1, 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 132521-70-1 as follows.

A mixture of 6-(4-methylpiperazin- 1 -yl)nicotinicacid (50 mg, 0.226 mmol), tert-butyl 2-amino-4-(thran-3- yl)phenylcarbamate (62 mg, 0.226 mmol) and EDCI (95 mg, 0.5 mmol) in pyridine (5 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE) and extracted with EA to afford crude (170 mg, crude).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,132521-70-1, its application will become more common.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, 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, HPLC of Formula: C7H7Br2NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H7Br2NO

General Procedure 2: Formation of an imidazole by sequential treatment of an amidine with LiHMDS and a heteroaryl-halomethylketone in THF followed by dehydration of the intermediate hvdroxyimidazoli?e in hot acetic acid.; A 1.0 M solution of LiHMDS in THF (Aldrich Chemical Co., 1.0-1.2 equiv, or 2.2 equiv when the heteroaryi-halomethyfketone is a hydrobromide salt) is added dropwise to a solution of the amidine (1.0 equiv) in anhydrous THF (generally 2-4 mL/mmol amidine) at -20 0C to 50C under nitrogen and the resulting solution stirred at about 0 0C for 10-30 min. A solution of the haloketo?e (1.0-1.5 equiv, in equal or greater amount relative to the lithium base) in anhydrous THF (1-3 mL per mmol) is added in one portion. The resulting mixture is stirred in an ice bath for 10-30 min and then at RT for at least 30 min. Water and organic solvent (usually EtOAc or DCM) are added and the product is isolated by extraction into the organic layer which is dried and concentrated. The resulting crude product, which generally contains hydroxy-imidazoline, the target imidazole, and unreacted amidine (HPLCMS analysis) is dissolved in acetic acid (5-25 mUmmol) and heated at 60-1000C for 20-60 min (HPLCMS showing disappearance of the hydroxy-imidazoline peak). This mixture is concentrated, and the crude product isolated by extraction using aqueous NaOH and organic solvent (usually EtOAc or DCM), and residual amidine removed by washing with aqueous citric acid. If not otherwise specified, the product was purified by SGC (gradient of MeOH in DCM, 0.5% NH4OH). In the following Example section, compounds of formula I are designated as Example 1, Example 2, and so on, whereas the corresponding synthetic intermediates are designated Preparation 1 A , Preparation 1 B, or Preparation 2A; Example 4; i-(4-(4-fpvridin-2-vO-1 -fpyrimidin-5-vl)-1 H-imidazol-2-vltohenvl)-1 H-pvrrolof2.3-biDvridine; According to General Procedure 2, NI-(pyrimidi?-5-yl)-4-(1H-pyrrolo[2l3-b]pyridin-1- yl)benzamidine (447 mg, 1.42 mmol) and 2-bromo-1-(pyridin-2-yl)ethanone hydrobromide (400 mg, 1.42 mmol) gave the title substance as a yellow solid. Yield 80 mg, 13.5% of theory. 1H NMR (CDCI3) delta 9.24 (s, 1H), 8.77 (s, 2H)1 8.58 (m, 1H), 8.35 (del, 1H1 J = 1.7, 4.6), 8.13 (d, 1H, J = 7.9), 7.95 (dd, 1H, J =1.5, 7.7), 7.90 (s, 1H), 7.87 (m, 2H), 7.77 (m, 1H), 7.57 (m, 2H), 7.52 (d, 1H, J = 3.7), 7.20 (m, 1H), 7.13 (dd, 1H1 J = 5.0, 7.9), 6.64 (d, 1H, J = 3.7). MS (AP+) m/beta 416 (MH+). IC50 = 13.6 nM

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4117; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109880-43-5, 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.109880-43-5, name is Methyl 4-chloro-6-(hydroxymethyl)picolinate, molecular formula is C8H8ClNO3, molecular weight is 201.61, as common compound, the synthetic route is as follows.

1.5 g of compound 13 (7.4 mmol, 1 eq.) are dissolved in 200 mE dichloromethane and 3 mE triethylaminc are added (22.2 mmol, 3 eq.). Then 0.87 mE of mesyl chloride is added (11.1 mmol, 1.5 eq.) slowly and a progressive yellow coloring of the mixture is observed. The reaction progress is followed by CCM and stopped after 30 mm. 100 mE of a saturated solution of NaHCO4 are added and the organic phase is washed with water (up to pH=7) and brine. The organic solution is then dried on Na2SO4 and evaporated to give 2 g of a yellow oil of compound 14 used without thrther purification (quantitative yield). ?H-NMR (300 MHz, CDC13) oe (ppm)=8.1 (s, 1H),7.68 (s, 1H), 5.40 (s, 2H), 4.01 (s, 3H), 3.17 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 109880-43-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ECOLE NORMALE SUPERIEURE DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE CLAUDE BERNARD LYON I; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; MAURY, Oliver; GIRARD, Eric; ENGILBERGE, Sylvain; RIOBE, Francois; (76 pag.)US2018/362550; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15862-50-7, 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. 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine. A new synthetic method of this compound is introduced below.

Step 2 Scheme 38:a bTo a solution of a ( 6.8 g , 29 mmol ) in 78 mL of EtOH and l OmL of H20 was added 0.8 mL of cone. HC1 and iron powder ( 49 g ,174 mmol ) with stirring. The resulting solution was heated at 80C under a nitrogen atmosphere for 3 hrs and cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated to afford b (5.1 g, 86%) as a brown-yellow residue, which was used directly to next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENZYME CORPORATION; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; MAZITSCHEK, Ralph; CLARDY, Jon, C.; WIRTH, Dyann; WIEGAND, Roger; URGAONKAR, Sameer; BANIECKI, Mary, Lynn; CORTESE, Joseph; CELATKA, Cassandra; XIANG, Yibin; SKERLJ, Renato; BOURQUE, Elyse, M.j.; WO2011/53697; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 717843-51-1 ,Some common heterocyclic compound, 717843-51-1, molecular formula is C7H8BrNO, 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) Synthesis of 3-bromo-5-chloro-2-methoxy-4-methylpyridine 3-bromo-2-methoxy-4-methylpyridine (100 mg) was added to DMF (575 muL). NCS (72.5 mg) was added to the solution, and the mixture was stirred at 80 C. for three hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (100 mg). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.51 (s, 3H), 3.98 (s, 3H), 8.02 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,717843-51-1, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem