Tag: M.W:200-300

Reference of 1159812-31-3, Adding some certain compound to certain chemical reactions, such as: 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine,molecular formula is C7H6BrN3, 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 1159812-31-3.

To a solution of 7-bromo-2-methyl-[l,2,4]triazolo[1,5-a]pyridine (4.40 g, 20.7 mmol) and diphenylmethanimine (5.64 g, 31.1 mmol) in l,4-dioxane (60 mL) were added Pd2(dba)3 (952.2 mg, 1.04 mmol), BINAP (1.29 g, 2.07 mmol) and Cs2C03 (13.52 g, 41.50 mmol). The mixture was stirred at 100 C for 4 hours under N2 atmosphere, and concentrated in vacuo. The residue was diluted with water (200 mL) and DCM (100 mL), and the separated aqueous layer was extracted with DCM (100 mL c 2). The combined organic layers were washed with water (100 mL c 2), and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/5 to 1/2) to give the title compound as brown oil (6.48 g, yield 100%).MS (ESI, pos. ion) m/z: 313.1 [M+H]+.

According to the analysis of related databases, 1159812-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-51-3 ,Some common heterocyclic compound, 884494-51-3, molecular formula is C6H3FINO2, 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 suspension of 2-fluoro-4-iodonicotinic acid (896 mg, 3356 mumol) in 6M hydrochloric acid (13423 mul, 80540 mumol) was heated at 100 0C. After 5 min, the reaction became a solution, and then a precipitate appeared. The reaction mixture was stirred 60 min at 100 0C and then cooled to room temperature. Filtration afforded 2- hydroxy-4-iodonicotinic acid (710 mg, 2679 mumol, 80% yield). MS (ESI pos. ion) m/z: 248(M+H-H2O). Calc’d exact mass for C6H4INO3: 265.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-51-3, its application will become more common.

Reference:
Patent; Amgen Inc.; WO2006/116713; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, name: 5-Bromo-N2-methylpyridine-2,3-diamine, blongs to pyridine-derivatives compound. name: 5-Bromo-N2-methylpyridine-2,3-diamine

To a solution of 5-bromo-N2-methylpyridine-2,3-diamine (14 g, 69 mmol) in DMF (702 mL) at room temperature was added CDI (29 g, 180 mmol). The reaction mixture was stirred for 16 h. LCMS analysis of the crude reaction mixture showed that the reaction was not complete, and the resultant residue was re-dissolved in THF and CDI (11.2, 69 mmol) was added. The reaction mixture was stirred at 60 C for 16 h. The reaction mixture was quenched with water and diluted with Et2O. The suspension was filtered and the resulting solid was washed with Et2O and dried under vacuum to yield the title compound as a black solid (15.8 g, 35.7 mmol), which was used in the next step without further purification. MS (ESI): mass calcd. for C7H6BrN3O, 226.97; m/z found, 227.0 [M+H]+.

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHROVIAN, Christa C.; LETAVIC, Michael A.; RECH, Jason C.; RUDOLPH, Dale A.; JOHNSON, Akinola Soyode; STENNE, Brice M.; WALL, Jessica L.; (533 pag.)WO2018/67786; (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.89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.HPLC of Formula: C6H6INO

Preparation 94 To a suspension of 3-iodo-4-methoxypyridine (0.62g), 3-nitrophenylboronic acid (0.57g) and tetrakis(triphenylphosphine)palladium(0) (152mg) in dimetoxyethane (10ml) was added aqueous sodium carbonate (2M, 3.43ml) and the mixture was stirred at 60C for 6 hours. The mixture was diluted with ethyl acetate and washed with aqueous sodium hydroxide (1N) and brine. The separated organic layer was dried over magnesium sulfate and evaporated. The residue was purified with silica gel (25g) column chromatography and eluted with 40-80% ethyl acetate in n-hexane to give 3-(4-methoxypyridin-3-yl)nitrobenzene (84mg). APCI-mass;m/z231(M+H+) 1H-NMR(DMSO-d6): delta;3.90(3H,s), 7.24(1H,d,J=5.8Hz), 7.75(1H,t,J=8.0Hz), 8.00 (1H,d,J=8.0Hz), 8.24(1H,dt,J=8.2Hz,1.1Hz), 8.35(1H,t,J=1.0Hz), 8.48(1H,s), 8.53(1H, d,J=7.6Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89640-55-1, 3-Iodo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1264820; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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. 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, molecular formula is C5H4BrIN2, 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 mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%).

According to the analysis of related databases, 915006-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); 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. 69422-72-6, name is 2,4,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, 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: 2,4,6-Trichloronicotinic acid

EXAMPLE 3D /erf-butyl 2-(2,4,6-trichloronicotinamido)ethylcarbamate A solution of the product of EXAMPLE 3C (6.0 g, 26.5 mmol) in dichloromethane (150 mL) was treated at 0C with 2 drops of N-dimethy lformamide. Oxalyl chloride (6.73 g, 53 mmol) was added dropwise over 30 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. A solution of the acid chloride (4.5 g, 18.4 mmol) in 60 mL of dry dichloromethane was added dropwise over 1 hour to a solution of tert-butyl 2-aminoethylcarbamate (5.9 g, 36.8 mmol) and triethylamine (3.7 g, 36.8 mmol) in 40 mL of dry dichloromethane at 0C and stirring was continued for 2 hours. The mixture was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 390 (M+Na+).

With the rapid development of chemical substances, we look forward to future research findings about 69422-72-6.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866775-18-0, 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 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate. This compound has unique chemical properties. The synthetic route is as follows.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 ml); Sodium hydroxide (2.0 M aqueous solution) (14.04 ml, 28.1 mmol) was added and the suspension was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water (100 ml) and then acidifed by the addition of 5.0M HCI(aq). The product was extracted into ethyl acetate (2 x 75 ml) and the combined organic extracts were washed with water (50 ml), brine (25 ml), dried (MgS04) and concentrated under reduced pressure to afford the title product as a yellow solid. H-NMR: 9400MHz, DMSO-d6) ? 13.24 (1 H, br s, C02H), 7.74 (1 H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1 , 287.1 [M+H]+

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38373; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 170165-79-4, 1,3-Di(pyridin-4-yl)benzene, 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, Quality Control of 1,3-Di(pyridin-4-yl)benzene, blongs to pyridine-derivatives compound. Quality Control of 1,3-Di(pyridin-4-yl)benzene

General procedure: A mixture of Zn(NO3)2 (0.15 mmol), 1,3-dpb and glu2- (0.1 mmol) was dissolved in 8 ml of DMF-MeOH-H2O (1 : 1 : 2, v/v). The final mixture was placed in a Parr Teflon-lined stainless steel vessel (15 ml) and heated at 110 C for3 days, colourless crystals were obtained (52% yield based on 1,3-dpb). IR (KBr, gamma/cm-1): 3425 (m), 3068 (w), 2848 (w), 2359 (m), 1580 (s), 1515 (s), 1394 (s), 1226 (s), 1156 (w), 1056 (s), 964 (w), 852 (w), 757 (m), 674 (m), 536 (m). Found (%): C, 59.06; H, 4.13; N, 6.41. Calc. for C21H18N2O4Zn (%): C, 58.96; H, 4.24; N, 6.55.

The synthetic route of 170165-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Jin-Song; Lei, Zhang; Xing, Hong-Long; Zhang, Xiao-Mei; Shi, Jian-Jun; He, Jie; Mendeleev Communications; vol. 23; 4; (2013); p. 229 – 230;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69045-83-6, 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. 69045-83-6, name is 2,3-Dichloro-5-(trichloromethyl)pyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 3 Conversion of 2,3-dichloro-5-(trichloromethyl)pyridine to 2,3-dichloro-5- (trifluoromethyl)pyridine. 2,3-dichloro-5-(trichloromethyl)pyridine (5 g, 18.84 mmole), iron(III) chloride (0.153 g, 0.942 mmole) and hydrogen fluoride (2.423 g, 85 mmole) in pyridine solution (70%) was added to an autoclave and heated to 175 C over night. The autoclave was cooled to 130 C and left for stirring additional 5 hours, followed by cooling to 25 C and opened carefully leaving gas phase through a Caustic Lye scrubber. The crude was dissolved in dichloromethane, washed with 1 M NaOH (aq) and water. The organic phase was removed by distillation and the product was obtained by distillation (3.0 g, 73 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-83-6, 2,3-Dichloro-5-(trichloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMINOVA A/S; ANDERSEN, Casper Stoubaek; WO2014/198278; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1241752-31-7, 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. 1241752-31-7, name is 5-Bromo-2-ethoxy-3-methoxypyridine. A new synthetic method of this compound is introduced below.

d. Preparation of Compound To a solution of known 2-ethoxy-3-methoxy-5-bromopyridine (100 mg, 0.34 mmol) in 1,4- dioxane ( 3.0 ml), trimethyl boroxine (80 mg, 0.69 mmol) and Pd(dppf)Cl2 (56.3 mg, 0.069 mmol) was added, followed by CsC03 (300 mg, 0.92 mmol). The mixture was degassed for 30 minutes, and then heated to 90 C for 16 hr. After cooling, the crude mixture was filtered on celite and extracted with EtOAc (3x), washed with NaCl, the organic layer was dried with Na2S04 and concentrated to give crude product . The crude product was purified by ISCO flash chromatography using 10% EtOAc in hexane, giving 50 mg compound (Yield: 84%). ‘H NMR (300 MHz, CDC13) delta: 7.52 (s, I H), 6.84 (s, IH), 4.45 (q, 2H), 3.82 (s, 3H), 2.21 (s, 3H), 1.39 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1241752-31-7, 5-Bromo-2-ethoxy-3-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem