Month: October 2020

10201-73-7 , The common heterocyclic compound, 10201-73-7, name is 2-Amino-4-methoxypyridine, molecular formula is C6H8N2O, 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.

Add (1.0 mmol, 0.188 g) to a 50 mL pear-shaped flask3-acetylcoumarin, (1.4 mmol, 0.174 g) of 2-amino-4-methoxypyridine, and (1.0 mmol, 0.254 g) of iodine as a catalyst. The mixture in the pear shaped bottle is at 110 CAfter stirring for 4 h, it was cooled to 70 C and stirred overnight. Then add 5mL of distilled water and 0.6mL of mass fraction of 45%Sodium hydroxide solution (adjust the pH of the solution to 12), the mixture is stirred at 100 C for 1 h, cooled to room temperature, and addedNeutralize with 0.3 mL of 10% by mass of dilute hydrochloric acid until a neutral solution is obtained. Extracted 3 times with dichloromethane (each time25 mL), combined with extract phase, dried over anhydrous sodium sulfate, concentrated to remove solvent, then column chromatography (eluent: V acetic acid)Ethyl ester/V petroleum ether = 1:2) isolated to give a brownish-yellow product 3-(7-methoxy-2-imidazo[1,2a]pyridine)-coumarinCalled HP2) (0.152g, yield 52.2%)

The synthetic route of 10201-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Li Yujin; Zhou Zichun; Gao Jianrong; Han Liang; Ye Qing; (18 pag.)CN109943092; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1008-91-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1008-91-9, name is 1-(Pyridin-4-yl)piperazine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture ofCu(NO3)23H2O (0.2 mmol, 48 mg), 1-(pyridin-4-yl)piperazine(0.2 mmol, 33 mg) and Na2C2O4 (0.4 mmol, 54 mg) inwater (2 ml), dimethylformamide (DMF, 2 ml) and methanol(2 ml) was adjusted to pH 2 by adding 0.1 M HNO3 and stirringwas carried out for 5 min. The mixture was then sealed ina 20 ml glass vial, heated at 373 K for 1 d and cooled slowly toroom temperature. Blue crystals of (I) were obtained in a yieldof 14% (11 mg, based on the copper salt). Elemental analysiscalculated for CuC13H15N3O8: C 38.57, H 3.73, N 10.38%;found: C 38.22, H 3.56, N 10.65%. FT-IR peaks (ATR cell, ,cm1): (NH) 2755 (br); (C N) 1670 (m); as(OCO) 1617(s), 1516 (m); s(CO) 1407 (m); s(CO)+(OCO) 1287 (s), 1219(w), 1144 (w), 1027 (w), 923 (w); (OCO) 790 (s). UV-Vis(diffuse reflectance, cm1): 14310.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1008-91-9, 1-(Pyridin-4-yl)piperazine.

Reference:
Article; Klongdee, Fatima; Boonmak, Jaursup; Youngme, Sujittra; Acta Crystallographica Section C: Structural Chemistry; vol. 74; 3; (2018); p. 300 – 306;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

581-45-3, Adding a certain compound to certain chemical reactions, such as: 581-45-3, 4-(Piperidin-4-yl)pyridine, 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, 581-45-3, blongs to pyridine-derivatives compound.

4-Nitrophenyl chlorofonnate (183 mg; 0.91 mmol) was added under an argon atmosphere, at 0C, to a solution of F2 (370 mg; 0.82 mmol) and DIPEA (287 ul ; 1.65 mmol) in CH2C12 (10 ml). The mixture was stirred at 0C for 30 minutes. 4-Piperidin-4-yl pyridine (186 mg ; 1.15 mmol) was added. The mixture was stirred for 16 hours and was purified by flash chromatography with increasingly polar solutions of EtOAc/CH2C12 (0-100% EtOAc) and then MeOH/CH2Cl2 (0-15% MeOH) to give RIO as a pale yellow solid (190 mg). Yield: 36 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,581-45-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/79805; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

62089-74-1, 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. 62089-74-1, name is 1-(Pyridin-4-ylmethyl)piperazine, molecular formula is C10H15N3, 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 4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]benzoic acid (0.08 g, 0.26 mmol) in a mixture of dichloromethane (4 mL) and DMF (0.20 mL) is added 1-(4-pyridylmethyl)piperazine (0.046 g, 0.26 mmol), PS-DCC (0.41 g, 0.52 mmol) and HOBT (0.035 g, 0.26 mmol). The mixture is stirred overnight at 45C in a closed tube (orbital stirring). Then PS-Trisamine is added (0.52 mmol) and the mixture is stirred for 4 hr at room temperature, filtrated, and washed three times with dichloromethane. The solvents are evaporated under reduced pressure and the residue is purified by biotage column chromatography (eluent: ethyl acetate/methanol 10:1) to give 0.020 g (0.04 mmol), 16% as white solid. ES+(m/z)= 476 [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. 62089-74-1, 1-(Pyridin-4-ylmethyl)piperazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; EP1609789; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 126325-46-0, name is 2-Amino-3-bromo-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. 126325-46-0

Preparation 1; N-(3-Bromo-6-methvl-pvridin-2-vn-acetamide; Acetic anhydride (21 mL, 223mmol) was added to a solution of 2-amino-3-bromo-6-picoline (10g, 53.46mmol) in dioxan (50ml_) and the mixture was stirred at 50C for 18 hours. The solvent was then evaporated under reduced pressure and the residue was diluted with saturated sodium hydrogen carbonate solution (150ml_). The precipitate was filtered off, washed with water and re-dissolved in dichloromethane, and the filtrate was neutralised to pH7 with saturated sodium hydrogen carbonate solution and extracted with dichloromethane (3x100ml_). The organic solutions were combined, washed with water, dried over magnesium sulfate and concentrated in vacua to give a white solid. Purification of the solid by column chromatography on silica gel, eluting with ethyl acetateiheptane, 75:25, afforded the title compound as a white solid in 75% yield, 9.2g.

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, 126325-46-0, 2-Amino-3-bromo-6-methylpyridine.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2006/11050; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 170886-13-2 as follows., 170886-13-2

Starting material 8d 5-Iodo-2-(trifluoromethyl)pyridin-4-ol:A 250 mL round bottom flask was charged 2-(trifluoromethyl)pyridin-4-ol (prepared as described in Tyvorskii, V. I., Bobrov, D. N. Chemistry of Heterocyclic Compounds 1997, 33, 1138-9; 42.7 mmol). MeOH (45 mL) was added, and the solution was cooled to 0 0C. Potassium carbonate (6.55 g, 47.4 mmol) was added, and the resulting mixture was treated with iodine (11.37 g, 44.8 mmol) in portions over 5 minutes. The resulting mixture was allowed to stir at 0 0C, with slow warming to room temperature. After stirring at room temperature overnight, the reaction was quenched with aqueous NaS2theta3, was acidifed withHOAc (10 mL), and was extracted with EtOAc (4x). The combined organics were washed with brine, concentrated, and purified by silica gel chromatography (gradient elution; Rf in70:30 hexanes:EtOAc = 0.30) to give a pale yellow solid (2.74 g, 22%) of -90% purity. M/Z = 288. 1H NMR (400 MHz, DMSO-D6) delta ppm 7.19 (m, 1 H) 8.80 (m, 1 H) 12.43 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 170886-13-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59238; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

630120-99-9 , The common heterocyclic compound, 630120-99-9, name is 5-(Benzyloxy)-2-bromopyridine, molecular formula is C12H10BrNO, 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.

(1) The compound (201 mg) obtained in Reference Example 1-1-(1), 4H-1,2,4-triazole (63.1 mg), copper (II) acetate monohydrate (76.0 mg), and cesium carbonate (744 mg) were suspended in N,N-dimethylformamide (4 mL), and the mixture was deaerated, so that the air in the container was purged with nitrogen. The mixture was stirred under microwave irradiation at 120C for 1 hour and then stirred in oil bath at 160C for 7 hours. The mixture was cooled to room temperature, and then subjected to removal of insolubles by celite filtration and washing with ethyl acetate. An aqueous solution of saturated ammonium chloride was added to the mixture of filtrate and washing solution, the mixture was shaken, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and then brine, and was separated by a phase separator, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate = 1:1 to ethyl acetate only) to give 5-phenylmethoxy-2-(1,2,4-triazol-1-yl)pyridine (129 mg) as a colorless powder.

According to the analysis of related databases, 630120-99-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; TANAKA, Hiroaki; BOHNO, Ayako; HAMADA, Makoto; ITO, Yuji; KOBASHI, Yohei; KAWAMURA, Madoka; (235 pag.)EP3418276; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

614-18-6, Adding a certain compound to certain chemical reactions, such as: 614-18-6, Ethyl nicotinate, 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, 614-18-6, blongs to pyridine-derivatives compound.

Nicotinic acid ethyl ester 4 (1.5g, 10mmol) was dissolved in15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (2g, 40mmol), after the addition was complete, it was stirred at room temperature for 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried andconcentrated to give the desired product 5 (1.1g, 78%), without purification into the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,614-18-6, its application will become more common.

Reference:
Patent; Jiangshu Alpha Biopharmaceuticals, Inc.; Jiangnan University; Nanjing Drum Tower Hospital; Feng, Bainian; Yang, Guijun; Tang, Chunlei; Wang, Guping; Jie, Desheng; (36 pag.)CN105481765; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

866775-09-9, Adding some certain compound to certain chemical reactions, such as: 866775-09-9, name is Methyl 3-amino-6-bromopicolinate,molecular formula is C7H7BrN2O2, 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 866775-09-9.

4.2 Preparation of methyl 3-amino-6-(1-triisopropylsilanyl-1H-pyrrolo-[2,3-b]pyridin-5-yl)pyridine-2-carboxylate 7.50 g of methyl 3-amino-6-bromopyridine-2-carboxylate, 12.10 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-pyrrolo-[2,3-b]pyridine, 8.18 g of sodium hydrogencarbonate and 2.27 g of PdCl2(PPh3)2 in 90 ml of dioxane and 15 ml of water are heated at 90 C. under nitrogen in a flask until the reaction is complete (HPLC check, about 7 hours). The cooled reaction solution is diluted with EA and washed 3 times with water. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 5-100% in 25 min), giving 8.40 g of methyl 3-amino-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-2-carboxylate as white solid (yield 56%, content 92%); MS-FAB (M+H+)=425.2; Rf (Esi1rod method): 3.10 min.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 866775-09-9.

Reference:
Patent; MERCK PATENT GMBH; Klein, Markus; US2013/210819; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1433822-19-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1433822-19-5, name is 8-Bromo-6-chloro-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A zeaclion vial was chaied with 8-bmhbzo-[l,24]ffi o[1 a]pyzidir (0.500 g, 2.15rtuml, Example 1, Step A 5-mcephthnpytidim2-ane (0335 2.15 nuriol, ArkPhami1,4-dioxam (10 niLX CsCO (1.40 g, 43] nutol), Xaxtp}rs (0.0522 g, 0.108 rtutiol) and Pd(dba)(0.03 g, 0.11 rturiol), The ieac&iivialwas fhslitd with iuetgen, capred, sthiud and heated to about12X C overnight. Thi reactionwas cccled tortandthendibatedwithDCM (10] niL) an1water(] L).Theoipiuelayerwas septnted,washe1withwater(S] nlL),brine(l0]iuL), aiil diied over NaSO4. After corcenhathig the exhact to drnss, the prcduct was pnifled via silica Iuistta¡Àccraplv elutir with a gradient of 2]-50% ECAc in pe1eum ether to Soid C?-chlcwa-N(Y(0.50 g, 703 %): LCJMS (Table 1, Metlodr)RL 1.7Smin,MS m&331 (M+H).

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, 1433822-19-5, 8-Bromo-6-chloro-[1,2,4]triazolo[1,5-a]pyridine.

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