Day: June 1, 2021

Electric Literature of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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.

To a solution of 5-bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 C, was added oxalyl dichloride (16.98 mL,194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reaction mixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm) Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; HOUSE, David; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (141 pag.)WO2017/50714; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 717106-69-9, 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. 717106-69-9, name is Methyl 2-(6-chloropyridin-3-yl)acetate. A new synthetic method of this compound is introduced below.

A mixture of 0.500 g (2.69 MMOL) of Preparatory Compound A and 479 mg (2.69 MMOL) of N-BROMOSUCCINIMIDE in 5 mL of carbon TETRACHLORIDE was treated with 5 mg of azo-bis-isobutyronitrile and was heated at reflux for four hours and was allowed to cool. The mixture was concentrated to dryness and the residue was chromatographed on silica gel (230-400 mesh) using 95/5 DICHLOROMETHANE/ETHYL acetate as eluent to afford 353 mg (50%) of Preparatory Compound S methyl bromo (6-CHLORO- 3-pyridinyl) acetate as an oil ; 1HNMR (CDCI3) 6 8.44 (d, 1H, J= 2.6 HZ), 7.98 (dd, 1 H, J = 8.3 Hz and J = 2.5 Hz), 7.38 (d, 1 H, J = 8.5 Hz), 5.33 (s, 1 H), 3.82 (s, 3H); MS (ES+) m/z 265 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717106-69-9, Methyl 2-(6-chloropyridin-3-yl)acetate, and friends who are interested can also refer to it.

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

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 101990-70-9, name is 5-(Chloromethyl)-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H8ClNO

3,7-Dimethyl-1H-purine-2,6(3H,7H)-dione (300 mg, 1.67 mmol) was dissolved in N,N-dimethylformamide (10 mL), and 5-(chloromethyl)-2-methoxypyridine (263 mg, 1.67 mmol), potassium iodide (332 mg, 2.00 mmol) and potassium carbonate (461 mg, 3.34 mmol) were added. The reaction solution was heated to 120C, stirred for 3 hours and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:1 petroleum ether / ethyl acetate, Rf = 0.2) to give 1-((6-methoxypyridin-3-yl)methyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione (20.0 mg) with a yield of 4%. 1H NMR: (400 MHz, CDCl3) delta 8.28(s, 1H), 7.78(d, J = 8.0 Hz, 1H), 7.51(s, 1H), 6.67(d, J = 8.0 Hz, 1H), 5.12(s, 2H), 3.99(s, 3H), 3.91(s, 3H), 3.57(s, 3H). MS-ESI calcd. [M + H]+ 302, found 302.

With the rapid development of chemical substances, we look forward to future research findings about 101990-70-9.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Lingyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (160 pag.)EP3299371; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 136888-21-6, 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.136888-21-6, name is 2-Chloro-5-fluoro-3-nitropyridine, molecular formula is C5H2ClFN2O2, molecular weight is 176.53, as common compound, the synthetic route is as follows.

In a high-pressure reactor, 85 g (0.5 mol) of 2,3-dichloro-5-fluoropyridine was added to 200 mL of ammonia water.Set the temperature to 180 C, high pressure reaction 24h,TLC detects the reaction of the raw material completely.The solvent was evaporated to give 2-chloro-5-fluoro-3-aminopyridine 65 g;2-chloro-5-fluoro-3-aminopyridine 65 g (0.45 mol)Placed in 900 mL round bottom flask in acetonitrile,Aqueous buffer solution 450mL (0.6M K2CO3-4×10-4M EDTA disodium salt) was added successively,Acetonitrile 350mL (3mol) and 30% H2O2 in water290mL (3mol),The reaction mixture was stirred at room temperature for 1 hour and extracted with ethyl acetate (3 x 300 mL).Combine organic layers,Dry with anhydrous Na2SO4,Remove the solvent under vacuum to obtain the product of sufficient purity 2-chloro-5-fluoro-3-nitropyridine65g;To a solution of 2-chloro-5-fluoro-3-nitropyridine 65 g (0.35 mol) in DMSO/H2O (9:1, 3500 mL) was added L-Proline 230g (2mol),Na2CO3 210g (2mol),NaN3 230g (3.5mol),Sodium ascorbate 350g (1.75mol) andCuSO4·5H2O500g (2 mol);The mixture was stirred in an oil bath at 70 C for 24 hours.Then pour the mixture into 10,000 mL of ice water.The solid product was filtered and crystallized to obtain 47 g of 2-amino-5-fluoro-3-nitropyridine.

Statistics shows that 136888-21-6 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-fluoro-3-nitropyridine.

Reference:
Patent; Mao Shen; Hu Yalun; Liu Guofeng; (11 pag.)CN107903266; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1121-76-2, 4-Chloropyridine 1-oxide, 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, COA of Formula: C5H4ClNO, blongs to pyridine-derivatives compound. COA of Formula: C5H4ClNO

Reference Example 110 4-Chloro-2-cyanopyridine 4-Chloropyridine N-oxide (7.53 g, 58.1 mmol) and N,N-dimethylcarbamoyl chloride (9.36 g, 87.0 mmol) were added to acetonitrile (200 ml), and trimethylsilyl cyanide (11.5 g, 116 mmol) was added dropwise thereto.. The mixture was stirred at room temperature for 18 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over magnesium sulfate.. The solvent was evaporated, and the residue was subjected to a silica gel (200 g) column chromatography.. The fractions eluted with n-hexane-ethyl acetate (3:1, v/v) were collected, concentrated to give the titled compound (8.05 g, 99 %) as a pale yellow oil.1H-NMR (CDCl3) delta: 7.54-7.56 (1H, m), 7.72(1H, s), 8.63 (1H, d, J = 5.3 Hz). IR(KBr): 2239, 1568, 1549, 1462, 1379, 1288, 1215, 844, 704 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1121-76-2, 4-Chloropyridine 1-oxide, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); 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.70416-53-4, name is 5-Formylnicotinonitrile, molecular formula is C7H4N2O, molecular weight is 132.12, as common compound, the synthetic route is as follows.COA of Formula: C7H4N2O

INTERMEDIATE 76 PREPARATION OF 5-[(1E)-3-OXOPROP-1-EN-1-YL]PYRIDINE-3-CARBONITRILE A mixture of 5-formylpyridine-3-carbonitrile (1.82 g, 13.78 mmol) and (formylmethylene)triphenylphosphorane (4.28 g, 14.06 mmol) in DMSO (15 mL) was stirred overnight at 120 oC under a nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (EtOAc-petroleum ether, 1:3) to afford the title compound (490 mg, 22%) as a white solid.1H NMR (300 MHz, CDCl3) delta 9.79 (d, J = 7.2 Hz, 1H), 8.99 (d, J = 2.1 Hz, 1H), 8.92 (d, J = 2.1 Hz, 1H) 8.14 (m, 1H), 7.52 (d, J = 15.6 Hz, 1H), 6.87-6.79 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,70416-53-4, 5-Formylnicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; DENALI THERAPEUTICS INC.; BONANOMI, Giorgio; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian; LESLIE, Colin Philip; LYSSIKATOS, Joseph P.; NAPOLITANO, Carmela; POZZAN, Alfonso; SUDHAKAR, Anantha; SWEENEY, Zachary K.; TONELLI, Federica; DE VICENTE FIDALGO, Javier; (232 pag.)WO2017/96301; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1211533-93-5, Adding some certain compound to certain chemical reactions, such as: 1211533-93-5, name is 5-Chloro-2-methyl-3-nitropyridine,molecular formula is C6H5ClN2O2, 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 1211533-93-5.

To a solution of 5-chloro-2-methyl-3-nitropyridine (26g, 15 1 mmol) in ethyl acetate (850mL) under nitrogen atmosphere was added SnC12.2H20 (136g, 603 mmol) at room temperature. The reaction mixture was heated to 85C for 3h. Concentration of the reaction mixture under reduced pressure afforded a pale yellow slurry which was basified with I N NaOH solution (520mL). The resulting mixture was diluted withdichloromethane (750mL) and stirred for 10 minutes. The mixture was then fi ltered through a celite pad to remove undissolved solids. The filtrate’s organic layer was separated, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude compound was purified by column chromatography on silica gel ( 100-200 mesh) using 0-35% ethyl acetate in petroleum ether to afford desired 5-chloro-2-methylpyridine- 3-amine (18 g) as a brown solid.

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. 1211533-93-5, 5-Chloro-2-methyl-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BOBKO, Mark, A.; DARCY, Michael, G.; EVANS, Karen, A.; FAITG, Thomas, H.; KAURA, Arun, Chandar; PENG, Xin; SARPONG, Martha, A.; SEEFELD, Mark, A.; SU, Dai-shi; WO2012/149102; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90902-83-3, 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. 90902-83-3, name is 3-Amino-2-bromo-5-chloropyridine. A new synthetic method of this compound is introduced below.

tert-Butyl N- [(iS)- 1- [3 -(5,5 -dimethyl- 1,3 ,2-dioxaborinan-2-yl)phenyl]but-3 -en-iyl]carbamate (0.339 g, 0.944 mmol), 2-bromo-5-chloropyridin-3-amine (0.196 g, 0.944 mmol), and 2.0 M aq Na2CO3 (2.36 mL, 4.72 mmol) were added to dioxane (8 ml) and the resulting solution was purged with a stream of Ar for 10 mi Pd(PPh3)4 (0.055 g,0.047 mmol) was added and the mixture irradiated on microwave at 120 C for 30 mm. The reaction was quenched with water (20 ml) and extracted with EtOAc (3 x 30 ml). The combined organic layers were washed with brine (15 ml), dried (Na2SO4), filtered and concentrated. The residue was purified by normal phase chromatography using DCM and 0-10% MeOH as eluents to afford tert-butyl N-[(1S)-1-[3-(3-amino-5-chloropyridin-2-yl) phenyl]but-3-en-1-yl] carbamate (0.375g, 106%) as a tan foam. MS(ESI) m/z: 374.3(M+H). ?H NMR (500MHz, CDC13) oe 8.08 (d, J=2.2 Hz, 1H), 7.60 – 7.52 (m, 2H), 7.48 -7.43 (m, 1H), 7.34 (d, J7.7 Hz, 1H), 7.07 (d, J1.9 Hz, 1H), 5.72 (ddt, J=17.1, 10.1, 7.0Hz, 1H), 5.21 – 5.09 (m, 2H), 4.93 (br. s., 1H), 4.81 (br. s., 1H), 3.94 (br. s., 2H), 2.63 -2.51 (m, 2H), 1.43 (br. s., 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90902-83-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, 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.13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.

To a solution of 5-bromopyridin-2-ol (1 g, 5.75 mmol) in DMF (10 mL) were added 2-iodopropane (4.9 g, 28.75 mmol) and K2CO3 (4 g, 28.75 mmol). The mixture was stirred at rt overnight. The mixture was diluted with water (20 mL) extracted with EtOAc (3×25 mL), the combined organic phase was washed with brine, dried over Na2SO4, concentrated and purified by prep TLC to give 5-bromo-1-isopropylpyridin-2(1H)-one (380 mg, 31%). 1H NMR (CDCl3): 1.35 (d, 6H), 5.65-5.75 (m, 1H), 6.48 (d, 1H), 7.30 (m, 1H), 7.41 (d, 1H).

The chemical industry reduces the impact on the environment during synthesis 13466-38-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (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.13228-40-5, name is 2-(2-Pyridyl)indole, molecular formula is C13H10N2, molecular weight is 194.2319, as common compound, the synthetic route is as follows.Safety of 2-(2-Pyridyl)indole

General procedure: A sealed tube was charged with 4 (0.20 mmol), 2 (0.30 mmol), CeCl3·7H2O (0.02 mmol). Then 2 ml of ethanol was added to the reaction system. The reaction mixture was stirred at 120 C. The reaction was monitored by TLC until the 4 was completely consumed (about 12h). The solvent was removed under reduced pressure. The residue was purified through column chromatography using silica gel to give 5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13228-40-5, 2-(2-Pyridyl)indole, and friends who are interested can also refer to it.

Reference:
Article; Feng, Cheng-Tao; Zhu, Hui-Zhi; Li, Zhong; Luo, Zaigang; Wu, Song-Song; Ma, Shi-Tang; Tetrahedron Letters; vol. 57; 7; (2016); p. 800 – 803;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem