Month: March 2022

Related Products of 889944-76-7, 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. 889944-76-7, name is 6-Chloro-4-methylpyridine-3-sulfonyl chloride. A new synthetic method of this compound is introduced below.

A mixture of 6-chioro-4-methyipyridine-3-sulfonyl chloride (0.25 g, 1.106 mmol) in THF (5 mL) was treated with Hunig’s Base (0.290 mL, 1.659 mmol), followed by dimethylamine (2.0 M in THF, 0.829 mL, 1.659 mmol) at room temperature. After 1 hour, the reaction was concentrated and the crude was purified by column chromatography (24g Si02, 0 to 100% EtO Ax-hexanes, gradient elution) to afford 6- chloro-N,N,4-trimethylpyridine-3-sulfonamide (213 mg, 0.908 mmol, 82 % yield). LCMS(M+H) = 234.9; LCMS RT = 0.79 min; (Column: BEH Cl 8 2.1 x 50mm; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: acetonitrile with 0.05% TFA; Temperature: 50 C; Gradient: 2-98% B over 1.7 min; Flow: 0.8 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,889944-76-7, 6-Chloro-4-methylpyridine-3-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TARBY, Christine M.; NORRIS, Derek J.; LO, Julian C.; AHUJA, Vijay T.; SEITZ, Steven P.; GAVAI, Ashvinikumar V.; TOKARSKI, John S.; RAJASAGI, Mohini; WICHROSKI, Michael; BROEKEMA, Matthias; (155 pag.)WO2019/213340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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-N2-methylpyridine-2,3-diamine, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-N2-methylpyridine-2,3-diamine

To a suspension of 5-bromo-N2-methylpyridine-2,3-diamine (510 mg, 2.51 mmol) in AcOH (20 mL) was added MeC(OEt)3 (1 mL) and the solution was warmed to 80 C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-25% THF/CH2Cl2 gradient) to afford the desired product. 1H NMR (400 MHz, CDCl3) delta 8.36 (d, J=1.8 Hz, 1H), 8.06 (d, J=1.9 Hz, 1H), 3.80 (s, 3H), 2.65 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Babaoglu, Kerim; Brizgys, Gediminas; Cha, Jake; Chen, Xiaowu; Guo, Hongyan; Halcomb, Randall L.; Han, Xiaochun; Huang, Richard; Liu, Hongtao; McFadden, Ryan; Mitchell, Michael L.; Qi, Yingmei; Roethle, Paul A.; Xu, Lianhong; Yang, Hong; US2013/281433; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 874-10-2, 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.874-10-2, name is 8-Methylimidazo[1,2-a]pyridine, molecular formula is C8H8N2, molecular weight is 132.16, as common compound, the synthetic route is as follows.

General procedure: imidazo[1,2-a]pyridine 1a (118mg, 1 mmol), benzene ( 2a, 1 mL), Pd(OAc)2 (5 mol%), Ag2CO3(5 mol%) and PivOH (1.2 eq) were stirred in DMF (2 mL) at 130 C equipped with oxygen bag for 20 h. After completion of the reaction (monitored by TLC),the water (10mL) was added. The aqueous solution was extracted with ethyl acetate (3×15 mL) and the combined extract was dried with anhydrous MgSO4.The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether : ethyl acetate=21) to give a pure sample of 3a (Yellowoil, 144 mg, yield 74%).

Statistics shows that 874-10-2 is playing an increasingly important role. we look forward to future research findings about 8-Methylimidazo[1,2-a]pyridine.

Reference:
Article; Wang, Shaohua; Liu, Wenjie; Cen, Jinghe; Liao, Jinqiang; Huang, Jianping; Zhan, Haiying; Tetrahedron Letters; vol. 55; 9; (2014); p. 1589 – 1592;,
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. 56673-34-8, name is 3-Bromo-6-mercaptopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 3-Bromo-6-mercaptopyridine

B8. 5-Bromo-pyridine-2-sulfonyl chloride; 2.0 g of 5-bromo-pyridine-2-thiol (compound C2) are dissolved in 40 ml of carbon tetrachloride and 8 ml of water. Subsequently, the suspension is cooled in an ice bath and chlorine gas is passed into the reaction mixture for 20 min (flow: 35 ml/min). Thereafter, nitrogen is passed into the yellow solution to remove excess chlorine. Subsequently, the mixture is diluted with 150 ml of dichloromethane and extracted with 50 ml of brine. The organic layer is separated, dried using Na2SO4, filtered with suction, and evaporated to dryness to afford 2.70 g of the title compound as light yellow needles. M. p. 8O0C. GC-MS: 254.8/256.8/258.8 (77:100:25; M+). TLC: Rf = 0.84 (dichloromethane/ethanol 20:1 parts by volume).

The synthetic route of 56673-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTANA Pharma AG; WO2007/39578; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 667932-24-3 , The common heterocyclic compound, 667932-24-3, name is 2-Ethynylpyridin-4-amine, molecular formula is C7H6N2, 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.

Preparation of 3- (2-methoxy-6-trifluoromethylphenyl)-5- (4-aminopyridyl) isoxazole To a solution of [N-HYDROXY- (2-METHOXY-6-TRIFLUOROMETHYLBENZENE)] carboximidoyl chloride (lg, 3. [94MMOL)] and 4-amino-2-ethynylpyridine (310mg, 2. [63MMOL)] in THF was added triethylamine [(550ML,] 3.94mmol). The reaction mixture was stirred at room temperature for one hour and then refluxed for three hours. The mixture was cooled to room temperature, ethyl acetate and water were added. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to yield the crude product. The final product [3- (2-METHOXY-6-TRIFLUOROMETHYLPHENYL)-5- (4-AMINOPYRIDYL)] isoxazole (609mg) was obtained by purification with flash chromatography with hexanes: ethyl acetate (4: 1).

The synthetic route of 667932-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2004/18463; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 132834-56-1, 1-(6-Chloro-5-(trifluoromethyl)pyridin-2-yl)piperazine, 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, 132834-56-1, blongs to pyridine-derivatives compound. Recommanded Product: 132834-56-1

4-(Thiophen-2-yl)butanoic acid (100 ??, 0.68 mmol), HOBt (1 10 mg, 0.816 mmol), TBTU (262 mg, 0.816 mmol), anhydrous triethylamine (152 ??, 1.08 mmol) and anhydrous DMF (2 mL) were placed in an oven-dried Schlenk tube under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes. A second Schlenk tube was prepared containing 1-(6-chloro-5- (trifluoromethyl) pyridin-2-yl)piperazine (218 mg, 0.816 mmol) and anhydrous DMF (1 mL) under a nitrogen atmosphere. The resulting solution was stirred until complete dissolution of the piperazine had occurred. The piperazine solution was then transferred, via a cannula, to the first Schlenk tube containing the carboxylic acid. The resulting solution was stirred under nitrogen and monitored by TLC. After 24 hours, the DMF was removed under reduced pressure and the resulting oil was acidified using a 0.1 M HCI solution. The aqueous mixture was extracted with DCM (20 mL, followed by 4 x 10 mL) and the organic layer washed with a saturated sodium bicarbonate solution (3 x 20 mL) and brine (3 x 20 mL). The organic layer was dried over magnesium sulphate and the solvent removed in vacuo. The residue was purified using flash chromatography (3:2, EtOAc:n-hexane) to obtain the desired product in a 68% yield. H NMR (300 MHz, CDCI3) ? 7.66 (d, J = 8.7 Hz, 1 H), 7.10 (dd, J = 5.1 Hz, J = 1 .2 Hz, 1 H), 6.92-6.89 (m, 1 H), 6.80-3.79 (m, 1 H), 6.46 (d, J = 8.7 Hz, 1 H), 3.72- 3.67 (m, 4H), 3.97-3.57 (m, 2H), 3.52-3.49 (m, 2H), 2.88 (t, J = 7.5 Hz, 2H), 2.31 (t, J = 7.5 Hz, 2H), 2.09-1.99 (m, J = 7.2 Hz, 2H). 3C NMR (75 MHz, CDCI3) 171.2, 158.9, 147.5, 144.2, 137.6 (q, J = 3.75 Hz), 126.8, 124.5, 123.2, 1 17.8 (q, J = 268.5 Hz), 1 12.0 (q, J = 33 Hz), 103.3, 44.7, 44.5, 44.1 , 40.7, 31 .9, 29.2, 26.9. MS (+ESI) calcd for C18 H19 CI F3 N3 O S m/z: [M + H]+, 418.0962; found 418.0953 [Diff(ppm) = -2.23].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,132834-56-1, its application will become more common.

Reference:
Patent; NATIONAL UNIVERSITY OF IRELAND, MAYNOOTH; STEPHENS, John; FINDLAY, John; KINSELLA, Gemma; MARTIN, Darren; DEVINE, Robert; VELASCO-TORRIJOS, Trinidad; WO2013/60860; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63237-88-7, 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 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Pyrazolo[1,5-a]pyridine-2-carboxylic acid (J. Het. Chem., 18(6), 1981, 1149-1152, at page 1152) (81.8 mg, 0.50 mmol) was dissolved in 1-methyl-2-pyrrolidinone (3 mL) and the solution treated with 1-hydroxybenzotriazole hydrate (74.3 mg, 0.55 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (115 mg, 0.60 mmol) and the mixture stirred at room temperature for 5 minutes. The mixture was then treated with the amine of preparation 18 (200 mg, 0.48 mmol) and N-ethyldiisopropylamine (155 mg, 1.20 mmol) and the reaction mixture stirred at room temperature for 48 hours. The reaction mixture was partitioned between ethyl acetate (75 mL) and water (75 mL) and the organic layer washed with water (3*50 mL) and 0.880 ammonia in water (100 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was triturated with ether to yield the title product as a white solid, 223 mg. 1H-NMR(DMSO-D6, 400 MHz): 1.70(m, 8H), 2.41(s, 3H), 3.87(m, 1H), 3.98(m, 1H), 6.94(m, 2H), 7.00(m, 1H), 7.07(m, 2H), 7.38(m, 2H), 7.65(d, 1H), 7.74(m, 1H), 8.00(m, 1H), 8.22(m, 2H), 8.62(m, 1H). MS ES+ m/z 542 [MNa]+

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2005/20626; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936841-69-9, 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 936841-69-9 as follows.

To a solution of 4-(trifluoromethyl)pyridine-2-carbonitrile (1.7 g, 9.88 mmol) in methanol (18 ml) was added sodium methoxide (25 wt% in MeOH) (2.1 g, 9.9 mmol, 2.3 ml) and the mixture stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness, the residue suspended in methylamine (33 wt% in EtOH) (25 ml, 200.9 mmol) to which was added methylamine hydrochloride (6.7 g, 99.2 mmol). The reaction mixture was heated in a closed high pressure vial at 90C overnight. After cooling, the mixture was concentrated and the residue treated with dichloromethane, filtered and the filtrate evaporated under reduced pressure. This material was dissolved in diethyl ether, treated with a 2M hydrochloric acid solution in diethyl ether under cooling, stirred at 5-10C for 20 minutes, then diluted with water. The layers were separated and the organic phase washed twice with water. The combined aqueous phases were basified to pH 12 by addition of an aqueous 30% sodium hydroxide solution under cooling, and the product thoroughly extracted with diethyl ether (4x). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford N,N’-dimethyl-4-(trifluoromethyl)pyridine-2-carboxamidine as an oil (0.70 g), which was used without further purification. LCMS (method 1 ): 218 (M+H)+, retention time 0.28 min. 9F-NMR (MeOD, ppm) -66.4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936841-69-9, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; EMERY, Daniel; BUCHHOLZ, Anke; (145 pag.)WO2017/16910; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 167884-17-5, 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. 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol. A new synthetic method of this compound is introduced below.

To a solution of imidazo[l,2-a]pyridin-5-ylmethanol (0.150 g, 1.01 mmol, 1 eq) in DMF (2 mL) was added ethyl 3-bromopropanoate (367 mg, 2.02 mmol, 2 eq), NaOH (121 mg, 3.04 mmol, 3 eq) and TBAI (3.74 mg, 0.010 mmol, 0.01 eq). The mixture was stirred for 16 h at 50C. The reaction was quenched with water (10 mL), the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgS04 and concentrated in vacuo. The residue was purified by prep-TLC (Si02, DCM/MeOH = 10/1, Rf = 0.42) to give ethyl 3-(imidazo[l,2-a]pyridin-5-ylmethoxy)propanoate (0.04 g, 13% yield, 80% purity) as a yellow oil, LCMS: m/z = 249.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; PIPELINE THERAPEUTICS, INC.; XIONG, Yifeng; SCHRADER, Thomas; CHEN, Austin; ROPPE, Jeffrey Roger; BACCEI, Jill Melissa; BRAVO, Yalda; (199 pag.)WO2019/241131; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84539-34-4 ,Some common heterocyclic compound, 84539-34-4, molecular formula is C5H4Br2N2, 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.

Example 77: 3-(benzenesuIfoiiyl)-7-bromo-1H-pyrrolo[3, 2-cjpyridin- 2-amine To a stirred and nitrogen degassed solution of 3,5-dibromopynchn-4-amine (CM 84539-34-4; 2.5 g, 9.92 mmol), tetrakis(triphenylphosphane) palladium (287 mg, 248 itmol) in anhydrous DME (20 mL) was added a solution of 2- (benzenesulfonyl)acetonitrile (CM 7605-25-9; 1.98 g, 10.92 nimol) and sodium hydride (992 mg, 24.81 mmol, 6o% dispersion in oil) in anhydrous DME (12 mL). The reaction mixture was heated under microwave irradiation at 130 C for 2 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organics were filtered and dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica, o-ioo% EtOAc / petroleum ether) to afford the title compound.?H NMR (400 MHz, DMSO-d6) 6 ppm 6.6 (br. s., 2 H) 7.40 – 7.64 (m, 3 H) 7.91 – 7.98 (m, 2 H) 8.i8 (s, 1 H) 8.54 (hr. s., 1 H) 11.57 (s, 1 H).MS ESi 354

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84539-34-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LTD; BARKER, Gregory; DAVENPORT, Richard; DOWNHAM, Robert; FARNABY, William; GOLDBY, Anne; HANNAH, Duncan; HARRISON, David; WILLEMS, Henriette; (390 pag.)WO2015/198045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem