Tag: M.W:200-300

Application of 934279-60-4, 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. 934279-60-4, name is 2-Chloro-5-(trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of 2-chloro-5-(trifluoromethyl)pyridine-3-carbaldehyde of step 1-1 in ethanol (60 ml) was dropwise added NaBH4 (2.90g, 0.077 mol) while stimng for 30 min at room temperature. After the reaction was terminated with a saturated ammonium solution, extraction with ethylacetate was carried out. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography to give 2-chloro-5-(trifluoromethyl)pyr’idin-3-yl-methanol (12.3g, 76%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934279-60-4, its application will become more common.

Reference:
Patent; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); 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. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone, molecular formula is C12H8ClNO, 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: 6318-51-0

To a stirred solution of N-((4-fluorophenyl)(pyridin-2-yl)methyl)piperidine-4-carboxamide (key Intermediate-TV) (0.150 g, 0.479 mmol) in DCE (3 mL) were added benzofuran-2- carbaldehyde (0.07 g, 0.479 mmol, 1 equiv), and acetic acid (0.0287 g, 0.479 mmol,at 0 C and the reaction was stirred at room temperature for ih. Then sodium triacetoxy borohydride (0.281 g, 1.43 mmol, 3 equiv) was added. After completion, the reactionwas quenched with water and pH was adjusted -7 with saturated NaHCO3 solutionextracted with CH2C12. The combined organic extract was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude compound was purifiedHPLC to afford 0.040 g of 1-(benzofuran-2-ylmethyl)-N-((4-fluorophenyl)(pyridin-2- yl)methyl)piperidine-4-carboxamide (Yield =19Title compound was prepared by reductive amination of (4-chlorophenyl)(pyridin-2-yl)methanone (1 g, 4.59 mmol) using the general methodology of Example-59 and afforded0.5 g of 1 -(4-chlorophenyl)-N-methyl- 1 -(pyridin-2-yl)methanamine (Yield = 47%).

With the rapid development of chemical substances, we look forward to future research findings about 6318-51-0.

Reference:
Patent; THE BROAD INSTITUTE, INC.; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOLSON, Edward; WAGNER, Florence, Fevrier; WEIWER, Michel; SCOLNICK, Edward; PALMER, Michelle; LEWIS, Michael; PAN, Jennifer, Q.; ZHANG, Yan-Ling; XU, Qihong; (323 pag.)WO2016/100823; (2016); 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. 100397-96-4, name is 1-(4-Bromophenyl)-2-(pyridin-4-yl)ethanone, molecular formula is C13H10BrNO, 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: 1-(4-Bromophenyl)-2-(pyridin-4-yl)ethanone

Step B 1-(4-Bromophenyl)-2-(4-pyridyl)-ethan-1,2-dione A mixture of 200 mg (0.725 mmol) of l-(4-bromophenyl)-2-(4-pyridyl)-ethanone (from Step A) and 81 mg (0.725 mmol) of selenium(IV) oxide, and 5.5 mL of glacial acetic acid was heated to 135 C. for 2 h. After being cooled to room temperature, the reaction mixture was partitioned between saturated aqueous potassium carbonate and ethyl acetate. The aqueous layer was extracted twice more more with ethyl acetate. The organic layers were combined and washed with water and brine and dried over anhydrous sodium sulfate. Volatiles were removed under reduced pressure and the residue was flash chromatographed over silica gel (gradient elution 2-4% MeOH in DCM) to yield 100 mg of the titled compound, homogeous by TLC; mass spectrum (CI) m/e 290, 292 (M+1)+.

With the rapid development of chemical substances, we look forward to future research findings about 100397-96-4.

Reference:
Patent; Merck & Co., Inc.; US5955480; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77837-09-3 ,Some common heterocyclic compound, 77837-09-3, molecular formula is C13H11NO3, 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.

A round-bottom flask was charged with methyl 6-oxo-l -phenyl- l ,6-dihydropyridine-3- carboxylate 12a (2.26 g, 9.87 mmol), THF (58.5 mL) and MeOH (14.6 mL). The resulting slurry was cooled to 0 C. A solution of LIOH (700 mg, 29.2 mmol) in water (29.2 niL) was added dropwise via cannula. After stirring for 5 minutes the ice bath was removed. The mixture was stirred at rt for 45 minutes and then at 35 C for 30 minutes. After cooling to rt, the mixture was acidified to pH 1 with 1 N HCl and extracted with EtOAc (3 times). The combined organic layers were washed with brine, dried (Na?SO4), filtered, and concentrated in vacuo to afford 1.95 g of a brown solid which was used without further purification,[128] A round-bottom flask was charged with 1.30 g of the brown solid, THF (35.8 niL) and MeOD (8.94 ml). A solution of NaOD (99,5 atom percent D, 1.86 ml, 40 wt. percent in D2O) was added. After stirring at rt for 1.5 h, the mixture was cooled to 0 C. acidified to pH 1 with DCl (35 wt. percent in D2O), and extracted with EtOAc (3times). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 1.31 g (100 percent) of the title compound 22 as a brown solid. 1H NMR (DMSOd6): delta 8.22 (d, J= 2.4, 1H), 7.91 (dd, J- 2.7, 9.1, 1H), 7.62-7,48 (m, 5H), 6.58 (d. ,/ = 9.44, 1H). MS (M+H): 216.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77837-09-3, its application will become more common.

Reference:
Patent; CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott L.; WO2010/65755; (2010); 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.1234616-25-1, name is 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.HPLC of Formula: C8H7BrN2

A mixture of 2′-amino-/V,/V-dimethyl-5′-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-[2,3′-bipyridine]-5-carboxamide (360 mg, crude), 4-bromo-l-methyl-pyrrolo[2,3- b]pyridine (103 mg, 0.489 mmol), Na2C03 (2 M in water, 1 mL) and Pd(dppf)Cl2 (36 mg, 0.049 mmol, 10 mol% ) in DME (5 mL) was stirred at 100 C for 16 h under N2 atmosphere. A black suspension was formed. Crude LCMS showed the purity ofproduct is 13% (Rt= 0.513 min; MS Calc?d: 372.1; MS Found: 372.8 [M+H]+). The reaction mixture was diluted with ethyl acetate (10 mL), dried over Na2S04, filtered and concentrated. The residue was purified by Combi Flash (90% EtOAc in pentane), then the impure product was purified by prep-HPLC (0.1% TFA as additive) and lyophilized to afford 2′-amino-/V/V-dimethyl-5′-( 1 -methyl- 1//- pynOlo[2,3-b]pyridin-4-yl)-[2,3′-bipyridine]-5-carboxamide (15.8 mg, yield: 9%) as a light yellow solid. LCMS (Shimadzu LCMS 2010, mobile phase: from 100% [water + 0.05% NH32O] and 0% [MeCN] to 5% [water + 0.05% NH32O] and 95% [MeCN] in 5.8 min, then under this condition for 1.1 min, finally changed to 100% [water + 0.05% NH32O] and 0% [MeCN] and under this condition for 0.09 min.) purity is 97.33%, Rt = 2.472 min; MS Calc?d.: 372.1, MS Found: 373.2 [M+H]+. NMR (400 MHz, CDCh) d 3.11 (3H, s, overlapped with H2O signal), 3.19 (3H, s, overlapped with H2O signal), 4.05 (3H, s), 6.72 (1H, d, J= 3.6 Hz), 7.29 (1H, d , J= 5.2 Hz), 7.40 (1H, d , J= 3.6 Hz), 7.98 (1H, d , J= 8.4 Hz), 8.04 (1H, dd, J= 8.0, 1.6 Hz), 8.37 (1H, s), 8.60 (1H, d , J= 6.4 Hz), 8.61 (1H, s), 8.80 (1H, d, J = 1.6 Hz). 10.27 (2H, br s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1234616-25-1, 4-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 194673-12-6, Adding some certain compound to certain chemical reactions, such as: 194673-12-6, name is Ethyl 6-oxo-2-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate,molecular formula is C9H10F3NO3, 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 194673-12-6.

A solution of ethyl 2-hydroxy-6-(trifluoromethyl)-3,4-dihydropyridine-5-carboxylate (14) (2.8 g, 11.8 mmol) and /V-bromosuccinimide (2.1 g, 11.8 mmol) in carbon tetrachloride (25 ml_) was heated at reflux overnight. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure to afford a yellow solid that was purified by flash chromatography (silica gel 24 g, eluent gradient: from petrol: EtOAc 9:1 to 1 :1. The desired fractions were concentrated under reduced pressure and repurified by column chromatography (S1O2, 10 g, eluent petrol:EtOAC 9:1 to 1 :1). The desired fractions were concentrated under reduced pressure to afford the title compound as a white solid (890mg, 32%); 1H NMR (500 MHz, Chloroform-d) d 8.01 (d, J = 9.2 Hz, 1 H), 6.87 (d, J = 9.2 Hz, 1 H), 4.39 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H); LCMS (4 minute method) product at Rt = 0.44 min and ES+ m/z 236.09 [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. 194673-12-6, Ethyl 6-oxo-2-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF SUSSEX; CARDIFF UNIVERSITY; UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED; WARD, Simon; BESWICK, Paul; PENNICOTT, Lewis; REUILLON, Tristan; CHUCKOWREE, Irina; VILLALONGA-BARBER, Carolina; PORTER, Roderick, Alan; (120 pag.)WO2019/166822; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1026796-81-5, 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. 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide. A new synthetic method of this compound is introduced below.

To a solution of N-(4-bromopyridin-2-yl) acetamide (250 mg, 1.16 mmol) and methyl iodide (0.094 mL, 1.51 mmol) in THF (4 mL) cooled to 0 C, sodium hydride (67 mg, 2.8 mmol) was added. The resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water (5 mL) and ethyl acetate (5 mL). The solvents were removed by concentration under reduced pressure. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 20 mL). The combined ethyl acetate layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the title compound (284 mg, 1.24 mmol, 69% yield). LCMS (ESI) m/e 229.0 (Bromo pattern) [(M+H)+, calcd for C8Hi0BrN2O, 228.99]; LC/MS retention time (method F): tR = 1.50 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); 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. 54718-39-7, name is 2,5,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, 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. Product Details of 54718-39-7

Step 1: 2,5,6-trichloronicotinamide (Intermediate P) 1,1′-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6-trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif., USA) in THF (400 mL), allowing gas evolution to cease between additions. The resulting mixture was stirred for 5 min and then was degassed with house vacuum and flushed with nitrogen (*2). The resulting mixture was heated to 50 C. for 60 min, then diluted with toluene (100 mL) and concentrated to half volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mL, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 min at room temperature, diluted with EtOAc (200 mL) and washed with water (3*100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 9:1 heptane/EtOAc (300 mL) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloronicotinamide.

With the rapid development of chemical substances, we look forward to future research findings about 54718-39-7.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); 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. 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, the common compound, a new synthetic route is introduced below. SDS of cas: 1026796-81-5

Step 2: N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)Cl2 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80 C. for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 min and then filtered. The organic solution was concentrated and the residue was recrystallized from EtOAc to give N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J=6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

The synthetic route of 1026796-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALLS, INC.; BHARATHAN, INDU T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CILLIS, Courtney A.; D’AMORE, Natalie; FLE,OMG, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Kirsta E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen g.; VOS, Tricia J.; XU, He; YE, Yingchun; (48 pag.)US2016/333007; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem