Day: April 15, 2022

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. 130284-52-5, name is 6-Bromo-5-chloropyridin-3-amine, molecular formula is C5H4BrClN2, 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. name: 6-Bromo-5-chloropyridin-3-amine

Pd2(dba)3 (176.56 mg, 0.19 mmol) and Xphos (183.83 mg, 0.39 mmol) were added to a solution of 6-bromo-5-chloropyridin-3-amine (800 mg, 3.86 mmol), 1 -methyl-3-(4,4,5,5-tetramethyl-i ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1203.52 mg, 5.78 mmol) and K3P04 (2.456 g,11.57 mmol) in dioxane/H20 (6/1, 20 mE) under an N2 atmosphere. The mixture was stirred at 1000 C. overnight. The reaction solution was filtered and the filtrate was concentrated to give a crude product. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 0/100). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford 1 57a (530 mg, 5 9.0% yield) as a yellow solid. ECMS (ESI) mlz M+i: 209.1.

With the rapid development of chemical substances, we look forward to future research findings about 130284-52-5.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1452-94-4, Adding some certain compound to certain chemical reactions, such as: 1452-94-4, name is Ethyl 2-chloronicotinate,molecular formula is C8H8ClNO2, 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 1452-94-4.

A toluene solution (300 mL) of ethyl 2-chloronictinate (5.57 g), phenylboronic acid (4.76 g), tripotassium phosphate (8.91 g), 1,1′-bis (diphenylphosphino) ferrocene-palladiumdichloride dichloromethane complex (439 mg) was stirred under reflux for 4 hours in a nitrogen atmosphere. Water (100 mL) was added to the reaction solution, and the reaction solution was separated. The obtained organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified with silica gel column chromatography (hexane/ethyl acetate=96/4 to 75/25) to give ethyl 2-phenylnicotinate (5.27 g) as an oil. MS m/z 229 [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. 1452-94-4, Ethyl 2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SUMITOMO DAINIPPON PHARMA CO., LTD.; FUSANO, Akira; KOBAYASHI, Tomonori; SAITO, Yasuhiro; KANAI, Toshio; (55 pag.)US2016/221948; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 72141-44-7 , The common heterocyclic compound, 72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, 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.

(e); 10.0 g (69.9 mmol) of crude 4-chloro-2-methoxypyridine obtained in Step (d) was dissolved in 100 ml of dimethylformamide, and 37.2 g (279 mmol) of N-chlorosuccinimide was added, followed by stirring at room temperature for 12 hours. 400 ml of water was added to terminate the reaction, followed by extraction with ethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 9.10 g (crude yield: 73%) of crude 4,5-dichloro-2-methoxypyridine. 1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.90(s, 3H), 6.85(s, 1H), 8.14(s, 1H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1167056-96-3 ,Some common heterocyclic compound, 1167056-96-3, molecular formula is C7H4BrClN2, 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 compound 221.4 (l . lg, 7.2mmol, l .Oeq) in dimethylformamide (20mL) at 0C, sodium hydride (0.5mL, 10.8mmol, 1.5eq) was added. Reaction mixture was stirred at 0C for 20min. Then, ethyl iodide (1.6mL, 10.8mmol, 1.5eq) was added. Reaction mixture was stirred at room temperature for 3h. After completion of the reaction, the reaction mixture was transferred into water to obtain the precipitate which was filtered, washed with water and dried well under vacuum to obtain 221.5. (0.9g, 12.91%). MS(ES): m/z 260.37 [M]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1167056-96-3, its application will become more common.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); 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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.SDS of cas: 866775-18-0

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A step 4) (300 mg, 1.003 mmol), N,N-dimethylprop-2-yn-1- amine (0.1 19 ml, 1.104 mmol) and copper(l) iodide (3.82 mg, 0.020 mmol) in 1 ,4- dioxane (1.500 ml) under nitrogen was treated with triethylamine (1.818 ml, 13.04 mmol) followed by Pd(PPh3)2CI2 (14.08 mg, 0.020 mmol) and stirred at 100C for 15 minutes. A further portion of Pd(PPh3)2CI2 (14.08 mg, 0.020 mmol) was added and stirring continued at 100C for 15 minutes. The mixture was poured into water and extracted with EtOAc. The organic portion was separated and washed with water, brine and dried using a phase separating column. The mixture was acidified to pH1 using 1 M HCI and the aqueous portion was separated and basified to pH7 using saturated sodium bicarbonate solution. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine and dried using a phase separating column. The solvent was removed under reduced pressure to afford the title compound; LC-MS Rt = 0.51 min [M+H]+ 302.4 ; Method 2minl_owpH.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren, Mark; WO2013/38381; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 688782-02-7, 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. 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7ClN2, 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-chloro-3-methyl-lH-pyrrolo[2,3-b]pyridine (1.1 g, 6.6 mmol) in Nu,Nu’- dimethylformamide (20 mL) was added NaH (166 mg, 6.93 mmol) at 0 C. The mixture was stirred at room temperature for 30 minutes and benzenesulfonyl chloride ( 1.2 g, 6.6 mmol) was added. After 2 hours, the reaction was complete and was partitioned between water and ethyl acetate. The organic phase was concentrated and was purified by flash chromatography on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate to provide the title compound. LC/MS m/z 307 (M+H)+.

According to the analysis of related databases, 688782-02-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 4434-13-3 ,Some common heterocyclic compound, 4434-13-3, 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.

To a stirred solution of 5-methylpicolinic acid (2.5 g, 18 mmol) in 50C12 (10 mL) was slowly added DMF (21.3 mg, 3 mmol). The resulting solution was heated to 72 oC for 12h. After cooling to room temperature, the mixture was diluted with toluene and concentrated to near dryness in vacuo. MeOH was added to the obtained oily residue. The contents were stirred for 2 h at 30 oC. After filtration, aq.15% Na2CO3 was added to the filter cake to adjust its pH to 7, and then washed with cold MeOH to afford the title compound (220 mg). MS (ES) m/z 186 (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. 4434-13-3, 5-Methylpicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; HUDSON, Ryan; BEAUSOLEIL, Anne-Marie; (616 pag.)WO2018/89261; (2018); 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.73406-50-5, name is Ethyl 3-hydroxypicolinate, molecular formula is C8H9NO3, molecular weight is 167.162, as common compound, the synthetic route is as follows.Formula: C8H9NO3

3-Hydroxy-picolinic acid (15.6 g, 42.1 mmol), ethanol (360 mL), benzene (100 mL) and 98% sulfuric acid (6 mL) were heated under reflux for 40 h. After evaporation of the ethanol and benzene, the residue was dissolved in water, neutralized with sodium bicarbonate, and extracted with chloroform. The organic layer was dried (MgS04), filtered, and then the solvent was evaporated to give ethyl 3-hydroxy-picolinate as a brown oily residue (11.0 g).A mixture of ethyl 3-hydroxy-picolinate (11.0 g, 65.8 mmol), ethyl bromoacetate (12.1 g, 72.4 mmol) and anhydrous potassium carbonate (11.8 g, 85.5 mmol) in acetone (120 mL) was heated under reflux for 15 h. After cooling, the inorganic material separated by filtration. The filtrate was dissolved in chloroform, washed with water, then brine and dried (MgSO4), filtered, and the solvent was evaporated to give a brown oily residue. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.7 g) as a yellow oil (13.7 g). Ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.6 g, 54.0 mmol) and sodium ethoxide (8. 08 g, 118.8 mmol) in toluene (200 mL) were heated under reflux for 18 h. After cooling, a precipitate was collected by filtration, dissolved in the minimum amount of hot water (about 300 mL), and acidified with acetic acid (6 mL). The resulting precipitate was filtered, and dried in vacuo to give ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate as a solid (7.0 g). Ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate (6.90 g, 25.8 mmol) was dissolved in 10% hydrochloric acid (50 mL), and heated under reflux for 3 h. Evaporation of the hydrochloric acid solution gave furo [3,2-b] pyridin-3 (2H)-one hydrochloride (9.0 g). A portion of the furo [3,2-b] pyridin-3 (2H) -one hydrochloride was converted to its free base by treatment with saturated sodium bicarbonate and extraction with chloroform in preparation for the following step. N, N-Diisopropylethylamine (1.08 g, 8.34 mmol) was added slowly to a solution of furo [3,2-b] pyridin-3 (2H) -one (1.40 g, 7.25 mmol) in dry dichloromethane (60 mL) under nitrogen at-10°r; C. Then trifluromethanesulfonic anhydride (2.45 g, 8.70 mmol) was added slowly. The mixture was warmed to RT, and stirred overnight. The reaction was quenched with water. The organic layer was washed with water and brine, dried (MgS04), and then the solvent was evaporated to give a brown oily residue, which was purified by flash chromatography using chloroform to give the sub-title compound (980 mg) as a light-brown oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/42538; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103577-66-8, (3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-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, COA of Formula: C9H10F3NO2, blongs to pyridine-derivatives compound. COA of Formula: C9H10F3NO2

Ph3PO (43.78 g, 157.5 mmol) was dissolved in toluene (100 mL) in a 500 mL three-necked flask and BTC(14.84 g, 50 mmol) was dissolved in toluene (60 mL) and placed in a 150 mL constant pressure dropping funnel,BTC was added dropwise at room temperature, and the temperature was raised to 60 ° C after completion of the dropwise addition.After incubation for 4 hours, 2-hydroxymethyl-3-methyl-4- (2,2,2-trifluoroethoxy) pyridine(33.15 g, 150 mmol) was dissolved in 75 mL of toluene and added at 40 ° C to precipitate a white solid. After the reaction was carried out for 2 hours, the reaction was stopped and the white solid was obtained by filtration to dryness 2-chloromethyl-3-methyl-4- (2,2,2-trifluoroethoxy) pyridine hydrochloride 40.01 g, product yield 97percent

The synthetic route of 103577-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Hainan Weikang Pharmaceutical (Qianshan) Co., Ltd.; Weng Yiyi; Su Weike; Wang Jincan; Wang Ningqing; Zhong Da; Zhu Zhixin; (27 pag.)CN107011252; (2017); A;,
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 49669-13-8, name is 2-Acetyl-6-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Acetyl-6-bromopyridine

A solution of l-(6-bromopyridin-2-yl)ethanone (2.9636 g, 14.82 mmol) in methanol (40 mL) at 0C was charged with sodium borohydride (1.682 g, 44.4 mmol) and then allowed to warm to room temperature. After 2.5 hours, the reaction mixture was diluted with dichloromethane (60 mL) and water (60 mL) and the layers were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield the title compound. Calc’d for C7H9BrNO [M+H]+: 204, Found: 204.

With the rapid development of chemical substances, we look forward to future research findings about 49669-13-8.

Reference:
Patent; MERCK & CO., INC.; WO2008/156726; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem