Tag: M.W:100-200

Reference of 16830-24-3 ,Some common heterocyclic compound, 16830-24-3, molecular formula is C8H9NO2, 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 solution of (NH4)25208 in water was added to a solution of methyl 2-methylpyridine-4-carboxylatein methanol at reflux. The resulting reaction mixture was then stirred at reflux. Aqueous work up andrecrystallization from DCM afforded the title compound as white solid. ?H-NMR (300 MHz, CDC13): oe7.60 (s, 2 H), 4.78 (s, 2 H), 3.93 (s, 3 H), 3.81 (s (br), 1 H), 2.61 (s, 3 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. 16830-24-3, Methyl 2-methylisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPITHERAPEUTICS APS; BOESEN, Thomas; LABELLE, Marc; YANG, Ying; SARASWAT, Neerja; DUDEKULA, Dastagiri; COOK, Cyril John; VAKITI, Ramkrishna Reddy; ZHANG, Rui; ULLAH, Farman; (316 pag.)WO2016/33169; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 126325-47-1, name is 6-Bromo-2-methylpyridin-3-amine. A new synthetic method of this compound is introduced below., SDS of cas: 126325-47-1

A solution of 6-bromo-2-methylpyridin-3-amine (24 g, 128 mmol) and AcOH (14.7 mL 257 mmol) in MeOH (200 mL) was cooled to 0C, Br2 (36.9 g, 230.9 mmol, 11.9 mL) was added and stirred at 0C for 5 hours. The mixture was quenched with saturated aqueous Na2S03 (500 mL), extracted with ethyl acetate (300 mL x 3). The organic layer was washed with brine (200 mL), dried over Na2S04, and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ethenethyl acetate = 2:1) to afford 4,6-dibromo-2-methylpyridin-3-amine.

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, 126325-47-1, 6-Bromo-2-methylpyridin-3-amine.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; MARIGO, Mauro; (142 pag.)WO2019/121840; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-35-7 , The common heterocyclic compound, 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

At room temperature, 400 ml of N,N-dimethylformamide was added to a 1 L three-necked flask to start stirring. Add 5_bromo-7-azaindole (30g, 0.15mol) and potassium tert-butoxide (25·6g, 0 · 23mol) to the reaction flask. After stirring and clearing, cool the ice bath to wait for the internal temperature. At 0 C, triisopropylsilyl chloride (43.3 g, 0.225 mol) diluted with 80 ml of tetrahydrofuran was initially added dropwise. After the addition is completed, the reaction is maintained at 0-5 C for 10-20 minutes. TLC control, the reaction is over. 300 ml of water was added to the reaction flask, and the mixture was stirred for 15 minutes. The aqueous phase was extracted with methyl tert-butyl ether (200 ml*2). The organic phase was combined and the organic phase was washed with 500 ml of saturated aqueous sodium chloride solution once. After drying over anhydrous sodium sulfate, the solvent is concentrated to obtain an oil, and 50 ml of methanol is added to precipitate a solid. The solid is vacuum filtered and dried to obtain a compound of the formula. Yield: 50.5 g, yield: 93.8%.

The synthetic route of 183208-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hongbozhiyuan Pharmaceutical Co., Ltd.; Zhuang Yinqiang; Peng Shaoping; Jiang Hui; (11 pag.)CN107434807; (2017); A;,
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.136117-70-9, name is Imidazo[1,2-a]pyridine-8-carbonitrile, molecular formula is C8H5N3, molecular weight is 143.1454, as common compound, the synthetic route is as follows.Product Details of 136117-70-9

Synthesis of 3-iodoimidazo [1 ,2-a]pyridine-8 -carbonitrile. To a stuffed solution of imidazo[1,2-a]pyridine-8-carbonitrile (1.2 g, 8.38 mmol) in dichloromethane (10 mL) was added N-iodosuccinimide (1.89 g, 8.38 mmol). LCMS monitored the reaction until the starting material consumed completely. The reaction mixture was dilutedwith dichloromethane and water. The separated organic layer was dried sodium sulfate, filtered and concentrated to give 3-iodoimidazo[1,2-a]pyridine-8-carbonitrile (1.8 g, 6.69 mmol, 80 % yield) as a brown solid. MS (ES+) C8H81N3 requires: 269, found: 270 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136117-70-9, Imidazo[1,2-a]pyridine-8-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES; BIFULCO, Neil, Jr.; BROOIJMANS, Natasja; HODOUS, Brian, L.; KIM, Joseph, L.; MIDUTURU, Chandrasekhar, V.; WO2014/11900; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 138116-34-4, (4-Aminopyridin-3-yl)methanol, 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, Product Details of 138116-34-4, blongs to pyridine-derivatives compound. Product Details of 138116-34-4

General procedure: To a solution of 2-aminobenzyl alcohol (1.0 mmol, 1.00 equiv) and MnO2 (3.0 equiv.) in dry CH2Cl2 (20 mL) were stirred for 18 h at room temperature. The completion of reaction was monitored by TLC analysis. After the completion of reaction solvent was evaporated under reduced pressure at 40C and taken up for next step without any purification. 50 mL of methanol was added to same round bottom flask and corresponding aryl amines (1.0 equiv.), isocyanides (1.0 equiv.) and pTSA (15 mol%) added sequentially and the reaction mixture was stirred at room temperature for 12-15h. After the completion of reaction (monitored by TLC), the solvent of reaction mixture was evaporated under reduced pressure at 45oC to afford a black residue which was purified by column chromatography on silica gel (230-400 mesh) by eluting with gradient solution of hexane/EtOAc to get pure compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,138116-34-4, (4-Aminopyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Dev, Kapil; Ramakrishna; Maurya, Saransh Wales; Siddiqui, Ibadur Rahman; Kant, Ruchir; Maurya, Rakesh; Tetrahedron Letters; vol. 58; 12; (2017); p. 1202 – 1206;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52313-50-5 ,Some common heterocyclic compound, 52313-50-5, molecular formula is C6H7N3, 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 mixture of 1-(4-benzyloxy-3-fluoro-phenyl)piperidin-4-one (4.17 g, 13.94 mmol) and DMFDMA (20 mL) in acetonitrile (10 mL) was heated with stirring at 90 C for 2 hrs. The resulting reaction mixture was concentrated in vacuo and the residue was dissolved in EtOH (40mL). To the solution was added pyridine-2-carboxamidine (1.8 g, 14.96 mmol) and potassium carbonate (4.1 g, 2992 mrnol) successively. After being heated with stirring at 90 C overnight, the resulting reaction mixture was cooled to rt, diluted with water (60 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by columnchromatography (eluting with 5% MeOH in DCM) to give 6-(4-benzyloxy-3-fluoro-phenyl)-2-(2-pyridyl)-7 , 8-dihydro-5H-pyrido [4,3-d]pyrimidine (2.33 g). ?H NMR (400MHz, CDC13):8.96 – 8.85 (m, 1 H), 8.69 (s, 1 H), 8.53 (d, 1 H), 7.89 (t, 1 H), 7.52 – 7.32 (m, 6 H), 6.98 (t, 1 H),6.85 (dd, 1 H), 6.77 – 6.63 (m, 1 H), 5.12 (s, 2 H), 4.38 (s, 2 H), 3.61 (t, 2 H), 3.28 (t, 2 H). MSobsd. (ESf) [(M+H)]: 413.

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. 52313-50-5, Picolinimidamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5398-44-7, 2,6-Dichloroisonicotinic acid, 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, 5398-44-7, blongs to pyridine-derivatives compound. Quality Control of 2,6-Dichloroisonicotinic acid

a) A solution of 2,6-dichloroisonicotinic acid (20.0 g, 104 mmol) in ethanol (250 mL) and H2SO4 (5 mL) is stirred at 80 C. for 28 h. The solvent is removed in vacuo and the residue is dissolved in EA, washed with sat. aq. NaHCO3 solution and water, dried over MgSO4, filtered and evaporated to give 2,6-dichloroisonicotinic acid ethyl ester (17.7 g) as a brownish solid; LC-MS: tR=1.31 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5398-44-7, its application will become more common.

Reference:
Patent; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Mueller, Claus; Nayler, Oliver; Steiner, Beat; Velker, Jorg; US2011/212998; (2011); 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.71469-93-7, name is Methyl 4-aminopyridine-2-carboxylate, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.Product Details of 71469-93-7

Example (Ik-130) N-[2-(2,2-Difluorocycloprop-1-ylcarbamoyl)pyrid-4-yl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide The reaction with methyl 4-aminopyridine-2-carboxylate (cf. WO 2001/074788) takes place analogously to the reaction procedure in Example (Ik-127) using: 486 mg (3.19 mmol) of methyl 4-aminopyridine-2-carboxylate in 26.8 ml of dichloromethane, 1056 mg (3.19 mmol) of 1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride, 428 mg of silver(I) cyanide in 26.8 ml of acetonitrile. The remaining residue is purified by means of column chromatography on silica gel using the eluent mixture cyclohexane:acetone (gradient). This gives 984 mg of methyl 4-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)pyridine-2-carboxylate (69%). 1H-NMR (400 MHz, d6-DMSO): delta=8.67 (d, 1H), 8.31 (s, 1H), 7.80 (d, 1H), 4.03 (s, 3H), 3.90 (s, 3H) ppm. HPLC-MSa): log P=3.01; mass (m/z)=447 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,71469-93-7, Methyl 4-aminopyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer CropScience AG; US2011/301181; (2011); 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. 132213-07-1, name is Imidazo[1,2-a]pyridin-6-ylmethanol, molecular formula is C8H8N2O, 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. Application In Synthesis of Imidazo[1,2-a]pyridin-6-ylmethanol

Q. TH-1435 To a O0C solution of imidazo[l,2-a]pyridinyl-6-methanol (76 mg, 0.51 mmol), TH- 1152 (150 mg, 0.34 mmol), and PPh3 (134 mg, 0.51 mmol), in anhydrous toluene (1.5 mL) was added DIAD (103 muL, 0.51 mmol). The reaction mixture was stirred for 5 min, allowed to come to RT, stirred 3h, silica was added to it and volatiles removed. The residue was purified by column chromatography using 2:1 Hexanes/DCM to 20% acetone/DCM a second column 0-50% acetone/toluene. The residue was triturated with EtOAc to provide TH-1435 as a yellow crystalline solid (65 mg). 1H NMR (400 MHz, CDCl3) delta 7.74 (d, J = 2.2 Hz, IH), 7.55 (dd, J= 16.2, 5.7 Hz, 2H), 7.29 (dd, J= 8.6, 2.4 Hz, IH), 6.99 (d, J= 9.2 Hz, 2H), 6.64 (d, J= 8.5 Hz, IH), 6.60 (d, J= 9.2 Hz, 2H), 6.18 (dd, J= 11.0, 4.4 Hz, IH), 4.38 – 4.24 (m, 2H), 3.79 – 3.68 (m, 5H), 3.66-3.60 (m, J= 13.5, 6.0 Hz, 4H), 3.37 – 3.25 (m, IH).

With the rapid development of chemical substances, we look forward to future research findings about 132213-07-1.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2009/140553; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 932-35-4, 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. 932-35-4, name is 3-Hydroxypicolinonitrile, molecular formula is C6H4N2O, 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.

Preparation XV 2-Cyano-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside A solution of 1.7 g (14.17 mM) of 2-cyano-3-pyridinol in 80 ml of acetonitrile is prepared and 4.3 g (18.3 mM) of silver oxide and 3 g of 13* molecular sieve are added with the exclusion of light. The mixture is stirred at 50 C. for 10 min, 6.5 g (18.3 mM) of 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosyl bromide are then added and the reaction mixture is maintained at 50 C. for 18 hours with stirring. The mixture is subsequently cooled to ambient temperature and filtered through a filtration aid. The filtrate is diluted with ethyl acetate, washed with water, an N sodium hydroxide solution and then water to neutral pH and finally dried over magnesium sulfate and concentrated under reduced pressure. The residual oil is crystallized by addition of ethyl ether. 0.89 g of the expected product is obtained in the form of beige crystals (yield=16%). 1H NMR (300 MHz; CDCl3) delta: 8.43 (m, 1H), 7.53 (m, 2H), 5.49 (t, 1H), 5.30 (d, 1H), 5.19 (m, 2H), 3.18 (m, 1H), 2.76 (m, 1H), 2.10 (m, 9H).

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 932-35-4, 3-Hydroxypicolinonitrile.

Reference:
Patent; Laboratoires Fournier S.A.; US2009/182013; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem