Day: April 20, 2022

Reference of 884494-35-3 ,Some common heterocyclic compound, 884494-35-3, molecular formula is C5H3ClFNO, 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.

tert-butyl 4-(2-chloroacetamido)piperidine-1-carboxylate (2.02 g, 7.3120 mmol) and 2-chloro-5-fluoropyridin-3-ol (1.08 g, 7.32 mmol) weredissolved in DMF (70 ml). Caesium carbonate (4.88 g, 15 mmol) was added and the mixture heated to 1 oooc for 18 hours. After cooling toroom temperature the mixture was partitioned between ethyl acetateand water and the organic phase washed with water. The organic layerwas then evaporated onto silica and purified by flash column5 chromatography eluting with 20 to 100% ethyl acetate/iso-hexane togive the title compound (2.19 g, 85% yield). 1H NMR (400 MHz, CDCb):o 7.80 (d, J=2.5 Hz, 1 H), 7.23 (dd, J=2.7, 9.0 Hz, 1 H), 4.70 (s, 2H), 4.43- 4.29 (m, 3H), 2.81 (m, 2H), 2.50 – 2.37 (m, 2H), 1.74 (dd, J=1.5, 11.6Hz, 2H), 1.50 (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,884494-35-3, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 182275-70-3 , The common heterocyclic compound, 182275-70-3, name is 2-Iodo-6-methoxypyridine, molecular formula is C6H6INO, 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.

tei -Butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2/-/)- carboxylate (Intermediate 7) (395 mg, 1.28 mmol) and Cs2C03 (1.03 g, 3.19 mmol) were added to a solution of 2-iodo-6-methoxypyridine (Intermediate 8) (300 mg, 1.28 mmol) in 1 ,4-dioxane (10 mL) and the resulting mixture was degassed under a nitrogen atmosphere for 20 min. (9,9-Dimethyl-9/-/-xanthene-4,5-diyl)bis(diphenylphosphane) (Xantphos, 36 mg, 0.06 mmol) and palladium(ll) acetate (29 mg, 0.13 mmol) were added and the resulting reaction mixture was stirred at 80 C for 18 h. The solvents were removed in-vacuo and residue was partitioned between H20 (80 mL) and EtOAc (60 mL). The aqueous layer was further extracted with EtOAc (60 mL) and the combined organic layers were dried (Na2S04) and the solvent was removed in-vacuo. The residue was purified by column chromatography (normal phase neutral activated alumina, 10 % to 12 % EtOAc in hexane) to give tert- butyl 6- methoxy-3′,6′-dihydro-2,4′-bipyridine-T(2’/-/)-carboxylate (310 mg, 84 %) as a gum. LCMS (System 3, Method D): m/z 291 (M+H)+ (ESI +ve), at 5.73 min, 202 nm.

The synthetic route of 182275-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEPTARES THERAPEUTICS LIMITED; BROWN, Giles; TEOBALD, Barry; TEHAN, Ben; (77 pag.)WO2019/243851; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2897-43-0, Adding some certain compound to certain chemical reactions, such as: 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine,molecular formula is C5H3Cl2N3O2, 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 2897-43-0.

Intermediate 3: 2,6-Dichloro-3,4-pyridinediamine; 2,6-dichloro-3-nitro-4-pyridinamine (881 mg, 4.24mmol) was taken up in ethanol (15ml) and tin(ll) chloride (3212mg, 16.94mmol) was added portion wise over 5min. The resulting pale yellow solution was allowed to stir at 50C under N2 for 3h, LCMS showed approx 60% conversion, the reaction was left for a further 3h, LCMS showed almost complete conversion. The reaction was allowed to cool to room temperature and was partitioned between NaHC03 (aq) (50ml) and EtOAc (50ml). The organic layer was dried using a hydrophobic frit, concentrated and dried in vacuo overnight to give the title compound as a yellow solid (734mg). LCMS (Method B): Rt = 0.57min, MH+ = 178

According to the analysis of related databases, 2897-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); 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. 52605-96-6, name is 2-Chloro-3-methoxypyridine, the common compound, a new synthetic route is introduced below. Product Details of 52605-96-6

The 2-chloro-3-methoxypyridine (2) (13 g, 90.6 mmol), from Step I, was stirred with 3-equivalents of sodium methoxide (14.7 g, 271.8 mmol) in dimethylformamide (100 mL) at 100 C. until completion of the reaction. The reaction mixture was then quenched with water and extracted with dichloromethane. The combined extracts were washed with water, concentrated and distilled (74 C.; 5 mm Hg) to give the product, 2,3-dimethoxypyridine (3), as a clear oil (7 g; 29% yield for two steps).1H NMR (300 MHz, CDCl3) delta 7.65 (dd, 1 H, J1=5.1 Hz, J2=1.5 Hz), 6.96(dd, 1 H, J1=7.5 Hz, J2=1.5 Hz), 6.76(dd, 1 H, J1=5.1 Hz, J2=7.7 Hz), 3.95 (s, 3 H), 3.80 (s, 3 H).

The synthetic route of 52605-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioNumerik Pharmaceuticals, Inc.; US2008/261919; (2008); 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. 178876-83-0, name is Methyl 6-amino-3-bromopicolinate, the common compound, a new synthetic route is introduced below. name: Methyl 6-amino-3-bromopicolinate

To a solution of 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3 g, 12.99 mmol) and trimethyl boroxine (1.8 mL, 2.99 mmol) in 1,4 dioxane (30 mL) was added K2CO3 (3.5 g, 25.97 mmol) under an argon atmosphere. To this was added PdCl2 (dppf) 2.CH2Cl2 (530 mg, 0.65 mmol) and stirred at 115C for 4 h. The reaction mixture was cooled to room temperature and water was added to residue. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.9 g, 88%).MS ESI (m/e): 166.8 [(M+H)+].1H NMR (DMSO, 400 MHz): <5 (ppm) = 7.31(d, J= 8.4 Hz, 1H), 6.53 (d, J= 8.36 Hz, 1H), 5.99 (s, 2H), 3.77 ( s, 3H), 2.21 (s, 3H). The synthetic route of 178876-83-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/92272; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 108118-69-0, 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. 108118-69-0, name is 2,6-Difluoropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 4-(tert~butoxycarbonyl-methyl-amino)-benzoic acid (70 mg, 0.28 mmol) in CHiCi2 (2 mL) was added l-chloro-N,N-2-trimethylpropenylamine (98 muL, 0.74 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6~difluoro-rhoyridin-3-ylamine (30 mg, 0.23 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150 0C for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5s4-6]pyridine-2- yl)-phenyl]-methyl-amine (50 mg, 0.21 mmol, 89%). ES MS (M+H+) – 244; Eta NMR (300 MHz, DMSO-d6): delta 8.24 (t, J – 7.7 Hz, 1 H); 7.89 (d, J = 8.4 Hz, 2 H); 7.18 (d, J = 8.4 Hz, 1 H); 6.68 (d, J = 8.5 Hz, 3 H); 2.76 (s, 3 H); HRMS m/z 244.0883 (C13H10FN3O + H+ requires 244.0881).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108118-69-0, 2,6-Difluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/155017; (2009); A2;,
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.89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, molecular weight is 221, as common compound, the synthetic route is as follows.name: 3-Iodopyridin-4-ol

General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89282-03-1, 3-Iodopyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Article; Park, Hee Jung; Kim, Ji-Eun; Yum, Eul Kgun; Kim, Young Hoon; Han, And Chang-Woo; Bulletin of the Korean Chemical Society; vol. 36; 1; (2015); p. 211 – 218;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60010-03-9, 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.60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, molecular weight is 207.01, as common compound, the synthetic route is as follows.

6-Chloro-2-((f?)-3-fluoro-pyrrolidin-1 -yl)-4-methyl-3-nitro-pyhdine (Intermediate compound)To a solution of 2,6-dichloro-4-methyl-3-nitropyhdine (6.5g; 31.4 mmol) and TEA (1 Og; 3eq) in acetonitrile (200ml) was added (f?)-(-)-3-fluoropyrrolidine hydrochloride (4.75g; 1.2eq). The mixture was stirred for 4h at rt, after which the reaction mixture was quenched with sat NaHCOs(aq) (300ml), diluted with water and and EtOAc. The layers were separeted and the waterlayer was extracted with EtOAc (3x15OmL) untill no UV(254nm) active material was extracted). The com- bined organic layers were washed with brine and dried over Na2SO4(s). Filtration and in vacuo concentration resulted in a quantitative yield 8.36g of the title compound as a yellow/orange oil.

Statistics shows that 60010-03-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-4-methyl-3-nitropyridine.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 824-51-1 , The common heterocyclic compound, 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H8N2, 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.

To a solution of 6-methyl-1H-pyrrolo[2,3-b]pyri- dine (500 mg) in dichioroethane (6 mE) were added aluminum chloride (1.09 g) and acetyl chloride (0.40 mE), and then the mixture was stirred at room temperature for 1 .5 hours. The reaction solution was poured into aqueous saturated sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether to give 1 -(6-methyl-1H-pyrrolo[2,3-b]pyri- din-3-yl)ethanone [REx(8-i)] (481 mg) as a yellow powder. APCI-MS mlz: 175 [M+H].

The synthetic route of 824-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding CO., LTD.; MITSUBISHI TANABE PHARMA CORPORATION; Iijima, Toru; Takahashi, Yoichi; Hirai, Miki; Sugama, Hiroshi; Togashi, Yuko; Shen, Jingkang; Xia, Guangxin; Wan, Huixin; US2015/232459; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, 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, 15862-50-7, blongs to pyridine-derivatives compound. Formula: C6H5BrN2O3

2nd Step Pd(PPh3)4 (60 mg) and tributyl (1-ethoxyvinyl)tin were added to a DMAc (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (69 mg) obtained in the 1st step, followed by microwave irradiation (Initiator, 180 C., 10 minutes, 2.45 GHz, 0-240 W). Saturated sodium hydrogen carbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 3:7). A light yellow solid of 1-(2-methoxy-5-nitropyridin-3-yl)ethanone (72 mg) was thus obtained. MS (ESI m/z): 197 (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,15862-50-7, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; MIZUMOTO, Shinsuke; KUBO, Yohei; NAKATA, Hiyoku; HAGIWARA, Shinji; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; MASHIKO, Tomoyuki; YAMAMOTO, Mari; US2014/309225; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem