Tag: M.W:100-200

Application of 62150-45-2 , The common heterocyclic compound, 62150-45-2, name is 4-Bromopyridine-2-carbonitrile, molecular formula is C6H3BrN2, 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.

Step 1. 4-Bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine 4-Bromopyridine-2-carbonitrile (1.0 g, 5.5 mmol, Synthonix) in MeOH (10 mL) was treated with sodium methoxide (25 wt percent in MeOH, 0.095 mL, 0.47 mmol) and the reaction was stirred for 1 hour. Ammonium chloride (0.37 g, 6.9 mmol) was added and the reaction was stirred for 4 days. Solvent was then removed in vacuo. Water (4 mL) and EtOAc (6 mL) were added, the mixture was saturated with solid NaCl, and the mixture was stirred overnight. The solid product was isolated by filtration and dried at 40° C. under vacuum overnight. The product was used below without further purification. To 4-bromopyridine-2-carboximidamide (0.50 g, 2.5 mmol) in DMF (5 mL) was added K2CO3 (0.52 g, 3.7 mmol) and 3-bromo-2-butanone (0.24 mL, 3.2 mmol). The reaction was stirred for 4 days. The reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with two further portions of EtOAc. The combined organic extracts were washed sequentially with water and saturated NaCl solution. The organic solution was dried over Na2SO4, filtered, and concentrated. The crude product was triturated with methyl tert-butyl ether (MTBE, 2 mL) and the solid product was isolated by filtration and dried under vacuum at 40° C. for 3 hours. Yield: 372 mg, 59percent. LCMS (M+H)+: 252.0/254.0.

The synthetic route of 62150-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Sparks, Richard B.; Shepard, Stacey; Combs, Andrew P.; Buesking, Andrew W.; Shao, Lixin; Wang, Haisheng; Falahatpisheh, Nikoo; (158 pag.)US2017/190689; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1628-89-3, Adding some certain compound to certain chemical reactions, such as: 1628-89-3, name is 2-Methoxypyridine,molecular formula is C6H7NO, 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 1628-89-3.

A: 2 mol of 6-methoxypyridine and 700 ml of a 22percent potassium chloride solution were added to the reaction vessel.1.2L mass fraction of 26percent heptane solution, control solution temperature to 15 ° C,Adding an aqueous solution, 6 mol of aluminum isopropoxide, controlling the stirring speed of 370 rpm, and continuing the reaction for 120 min; B: Then, 6 mol of antimony trichloride powder was added, the temperature was controlled at 26 ° C, the reaction was continued for 3 h, then the temperature was lowered to 8 ° C, allowed to stand for 50 min, and the solution was layered.The oil layer was separated and washed 5 times with a 15percent sodium sulfate solution.The solution was washed 8 times with a mass fraction of 77percent in xylene and recrystallized from a cyclohexene solution having a mass fraction of 86percent.The dehydrating agent was dehydrated with anhydrous sodium sulfate to obtain 216.038 g of the obtained N-methylpyridin-2-one, and the yield was 99.1percent.

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Kadifu Technology Co., Ltd.; Liao Runai; (4 pag.)CN108239022; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-77-5, 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. 1620-77-5, name is 5-Methylpicolinonitrile. A new synthetic method of this compound is introduced below.

Synthesis Example 1 Ethyl 5-methylpyridine-2-carboxylate STR24 200 ml of ethanol and 100 ml (1.88 mol) of concentrated sulfuric acid were added to 55.5 g of 5-methylpyridine-2-carbonitrile to form a homogeneous solution, followed by heating under reflux for 2 days. The reaction liquid was gradually poured into a saturated aqueous solution of sodium hydrogencarbonate under cooling with ice to neutralize the sulfuric acid, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure to give 78.1 g of a brown oil of the title compound as the crude product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1620-77-5, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US5789403; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72716-87-1 , The common heterocyclic compound, 72716-87-1, name is 2-Methoxyisonicotinaldehyde, molecular formula is C7H7NO2, 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.

Nitrosonitric acid (1 mL) was added dropwise to a solution of 2-methoxypyridine-4-formaldehyde (137 mg, 1.0 mmol) in trifluoroacetic anhydride (2 mL) at room temperature. The reaction mixture was stirred at 25 C for 3 days, and then was poured into ice-water mixture, followed by the addition of saturated sodium carbonate solution to adjust the pH value to exceed 10. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried and concentrated. The resulting residue was dissolved in toluene (5 mL), and toluene-p-sulfonic acid (5 mg) and glycol (105 mg, 1.7 mmol) were added. The reaction mixture was heated to reflux and reacted overnight. After cooled, the mixture was washed with saturated sodium carbonate solution and brine, dried, and concentrated under vacuum. The resulting residue was dissolved in methanol (10 mL), added Pd/C catalyst (20 mg), and introduced into hydrogen gas. The reaction system was stirred for 2 h under 1 atm hydrogen, then filtered to remove the catalyst, and concentrated under vacuum to remove the solvent. The residue was purified by column chromatography to obtain the title compound (15 mg, 8 %). 1H NMR (DMSO-d6): delta 9.31 (1H, s), 8.56 (1H, s), 7.42 (1H, s), 7.34 (1H, s), 6.55 (1H, s), 5.43 (2H, s), 5.30 (2H, s), 4.02 (3H, s), 2.04-1.91 (2H, m), 0.90-0.85 (3H, m).

The synthetic route of 72716-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57266-69-0, 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. 57266-69-0, name is 3-Chloropicolinic acid. A new synthetic method of this compound is introduced below.

To a solution of 3-chloropicolinic acid (20.006 g, 126.98 mmol) in toluene (200 mL) was added thionyl chloride (23.2 mL, 37.8 g, 317 mmol, 2.5 equiv.) and a catalytic amount of DMF (10 drops) and the mixture was heated at reflux for 1 h. After cessation of the gas evolution, the mixture was cooled and all volatiles were removed in vacuum to obtain to obtain the title compound (24.38 g, quant.) as a crude product, which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57266-69-0, 3-Chloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; DESHMUKH, Prashant; KOeRBER, Karsten; KAISER, Florian; KORDES, Markus; DICKHAUT, Joachim; NARINE, Arun; BANDUR, Nina Gertrud; VEITCH, Gemma; CULBERTSON, Deborah L.; NEESE, Paul; GUNJIMA, Koshi; WO2013/24006; (2013); 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. 34160-40-2, name is 6-Bromo-2-pyridinecarboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-2-pyridinecarboxaldehyde

Step 1: Synthesis of 2-bromo-6-(difluoromethyl)pyridine (0396) 3.81 g (23.6 mmol) of (diethylamino)sulfur trifluoride were added with ice cooling to a mixed solution of 2.00 g (10.8 mmol) of 6-bromopicolinaldehyde and 40 ml methylene chloride. After completion of the addition, said reaction mixture liquid was stirred for 2 hours with ice cooling. After completion of the stirring, the reaction was stopped by addition of 30 ml of saturated aqueous sodium hydrogen carbonate solution, and said reaction liquid was extracted with methylene chloride (2×30 ml). The organic layer obtained was washed with water, then dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=10:0 to 8:2), and 1.87 g of the desired compound were obtained as a white solid. (0397) 1H-NMR (CDCl3, Me4Si, 300 MHz): delta 7.73-7.58 (m, 3H), 6.58 (t, 1H, J=56 Hz).

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, 34160-40-2, 6-Bromo-2-pyridinecarboxaldehyde.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; NAKAYA, Yoshihiko; MASUZAWA, Yoshihide; FURUHASHI, Takamasa; MIYAKADO, Yuuki; HOTTA, Hiroyasu; INABA, Masamitsu; (76 pag.)US2016/221998; (2016); A1;,
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 14294-11-2, name is 1-(Pyridin-2-yl)thiourea. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 14294-11-2

According to Scheme 3 Step 4: A solution of 2-bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (23.8 mmol, 7.70 g) and of 1-(pyridin-2-yl)thiourea (26.2 mmol, 4.02 g) in EtOH (200 mL) was stirred under reflux overnight. The reaction was quenched with water (200 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield a brown solid. The resulting crude product was purified by flash chromatography over silica gel using DCM/AcOEt (98:2) as eluent to yield after evaporation 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methyl-N-(pyridin-2-yl)thiazol-2-amine (20.7 mmol, 7.80 g, 87%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=2.29 min; MS m/z ES+=378.

With the rapid development of chemical substances, we look forward to future research findings about 14294-11-2.

Reference:
Patent; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866546-07-8 ,Some common heterocyclic compound, 866546-07-8, molecular formula is C7H5ClN2, 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.

Step 4 ~~ Preparation of[3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-lH-pyrrolo[2,3- b]pyridin-3-yl)-methanol (131):[0206] A mixture of 5-chloro-lH-Pyrrolo[2,3-6]pyridine (4, 0.68 g, 4.46 mmol), 3-benzyloxy-2- cyclopropylmethoxy-benzaldehyde (130, 1.2 g, 4.25 mmol), and potassium hydroxide (0.68 g, 1 1 mmol) in methanol (50 mL) was stirred at room temperature for 4 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide compound as a white solid (131, 0.99g, 54%). MS(ESI) [M+H’]’ = 435.21.

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. 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PLEXXIKON, INC.; WO2008/80001; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 149489-32-7, 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 149489-32-7, name is 2-(Chloromethyl)-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 182; N-[6-Cyano-9-(3-fluoro-pyridin-2-ylmethyl)-2,3,4,9-tetrahydro-lH-carbazol-3-yl]- isobutyramideSuspend sodium hydride (60% suspension in mineral oil, 114 mg, 1.64 mmol) in dimethylformamide (7 mL) and cool to 0 0C. Add a solution of N-(6- cyano-2,3,4,9-tetrahydro-lH-carbazol-3-yl)-isobutyramide (Preparation 3) (385 mg, 1.37 mmol) in dimethylformamide (3.5 mL). After several minutes, warm the reaction to room temperature, and stir for 30 min, after which time add 2- chloromethyl-3-fluoro-pyridine (Preparation 60). Stir the reaction overnight and then dilute with ethyl acetate (100 mL). Wash the reaction mixture sequentially with brine (3 x 75 mL), water (75 mL), and brine (75 mL). Separate the organic layer, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Purify using flash chromatography [silica gel, gradient from 0: 100 to 20:80 (90: 10: 1 EPO dichloromethane:methanol:concentrated ammonium hydroxide) :dichloromethane] to provide 184 mg (38%) of the title compound as an off-white solid, m.p. = 213- 216 0C; MS: m/z 391 [C23H23FN4O + I]+; 1H NMR (300 MHz, DMSO-J6): delta 8.29- 8.31 (m, IH), 7.92 (d, /= 1.2 Hz, IH), 7.84 (d, / = 7.6 Hz, IH), 7.71-7.78 (m, IH), 7.58 (d, / = 8.5 Hz, IH), 7.38-7.44 (m, 2H), 5.56 (s, 2H), 3.99-4.04 (m, IH), 2.73- 3.00 (m, 3H), 2.49-2.55 (m, IH), 2.37 (septet, J= 6.8 Hz, IH), 1.96-2.00 (m, IH), 1.76-1.83 (m, IH), 1.01 (d, /= 6.8 Hz, 6H).

According to the analysis of related databases, 149489-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 156118-16-0, 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. 156118-16-0, name is 3-Amino-6-bromo-4-methylpyridine, molecular formula is C6H7BrN2, 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.

Step 2 [0611] To a suspension 6-bromo-4-methylpyridin-3 -amine (XV) (186 g, 994 mmol, 1.00 eq) and KOAc ( 1 15 g, 1.17 mol, 1.18 eq) in CHC13 (3.50 L) was added Ac20 (405 g, 3.97 mol, 3.99 eq) and the suspension was stirred at 25C for 1 h and then heated at 60-70C to reflux for an additional 2 h. After cooling the suspension to 25C, isopentyl nitrate (233 g, 1.99 mol, 2.00 eq) and 18-crown-6 (21 g, 79.5 mmol, 0.08 eq) was added and the suspension heated to reflux for 12 h. After cooling to 25C, the suspension was filtered and the filtrate was concentrated under reduced pressure to yield a residue that was treated with a suspension of potassium carbonate (450 g) in a solution of methanol and water (450 mL) at 0C for 3 h. The suspension was concentrated under reduced pressure to yield a residue that was extracted with EtOAc (1000 mL x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5-bromo-lH-pyrazolo[3,4-c]pyridine (XVI) (200 g, crude) as yellow solid. The crude product was used for the next step without any purification. NMR (DMSO- tf, 400 MHz) delta ppm 7.96 (s, 1H), 8.15 (s, 1H), 8.86 (s, 1H); ESIMS found for C6H4BrN3 mlz 198.3 (M+H).

According to the analysis of related databases, 156118-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (261 pag.)WO2017/23984; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem