Tag: M.W:100-200

Electric Literature of 1256805-54-5, Adding some certain compound to certain chemical reactions, such as: 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine,molecular formula is C6H7ClN2O, 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 1256805-54-5.

To a mixture of 6-chloro-4-methoxypyridin-3-amine (0.50 g, 3.1 mmol) andpotassium isothiocyanate (0.61 g, 6.3 mmol) in acetic acid (5 mL) at room temperature wasadded bromine (0.18 mL, 3.4 mmol) in acetic acid (2 mL) over 30 mm. The mixture wasstirred at room temperature for 16 h before additional potassium isothiocyanate (0.61 g, 6.3 mmol) and acetic acid (1 mL) were added. The mixture was stirred at room temperature for 24 h. To the mixture was added water (100 mL) and the mixture was stirred for 2 h. The insoluble material was collected by suction filtration and the filter cake was suspended in water (100 mL) and stirred for 2 h. The solid was collected by suction filtration and driedunder vacuum at 50 C to give 5-chloro-7-methoxythiazolo[5,4-bjpyridin-2-amine (0.70 g,3.1 mmol, 100% yield) as atan solid. MS (ESI)m/z: 215.9 [M+Hf 1H NMR (500 MI-Tz, DMSO-d6) oe 7.74 (br s, 2H), 7.02 (s, 1H), 3.94 (s, 3H).

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. 1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARPENTER, Joseph E.; BROEKEMA, Matthias; FENG, Jianxin; LIU, Chunjian C.; WANG, Wei; WANG, Ying; (244 pag.)WO2019/89670; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-46-4, 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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 5-chloro-3-methylpicolinamide The title compound was synthesized according to Method AA starting from 5-chloro-3-methylpicolinic acid (intermediate 6). MS m/z=171.1 [M+H]+. Calculated for C7H7ClN2O: 170

According to the analysis of related databases, 886365-46-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); 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.160590-36-3, name is 2-Methoxy-3-nitro-4-methylpyridine, molecular formula is C7H8N2O3, molecular weight is 168.15, as common compound, the synthetic route is as follows.Formula: C7H8N2O3

Sodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3- nitropyridine (250 g, 1.49 mol) in acetic acid (1.5 L) at ambient temperature and then Br2 (639 g, 4.00 mol) was added dropwise (30 min). After addition, the mixture was heated at 80 C for 12 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled (0 C) and quenched by sequential addition of 10% aqueous (1.5 L) and saturated aqueous Na2S03 (1.5 L). The resulting solid was collected by filtration washed with water, and dried under reduced pressure to give the title compound (302 g, 82.2% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-t 6): delta 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,160590-36-3, 2-Methoxy-3-nitro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HSIAO-WEI TSUI, Vickie; HEWITT, Michael, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (251 pag.)WO2016/77375; (2016); 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. 116241-61-3, name is 2-Fluoro-6-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Fluoro-6-methoxypyridine

A Schlenk flask with a stir bar was charged with NaOMe (4.7g, 87mmol) and sealed with a rubber septum, and THF (200mL) was added via cannula. Under N2(g) atmosphere, 2,6-difluoropyridine (5.0g, 43mmol) was added dropwise to the stirring solution via syringe to form 2-(methoxy)-6-fluoropyridine. This reaction was stirred overnight (approximately 12h) then THF was removed under reduced pressure. The flask containing crude product was evacuated and under positive N2(g), approximately 100mL of DMF was added, followed by the addition of imidazole (3.575g, 52.5mmol) and NaH (1.9g, 160mmol) at 0C. The flask was allowed to warm to room temperature and with positive nitrogen flow, a reflux condenser was attached and the flask was heated to 80C overnight with stirring. The reaction flask was cooled to room temperature, the DMF was removed from the mixture via rotary evaporator, and the remaining reaction mixture was transferred to a separatory funnel with 25mL CH2Cl2. The organic phase was washed with water (25mL x 3), dried over MgSO4, filtered, and the filtrate was concentrated to dryness via rotary evaporator. The crude Im-pyOMe was dissolved in 200mL of DMF and ethyl bromide (5.2g, 48mmol) was added dropwise with stirring. Under positive pressure of N2(g), a reflux condenser was attached and the flask was heated to 120C overnight. The reaction flask was cooled to room temperature and the red oily product was obtained after solvent removal. Upon column chromatography purification with 90:10 ratio of MeOH: CH2Cl2, 42% (5.233g, 18.4mmol) of product was obtained. 1H NMR (360MHz, CDCl3, ppm): delta 11.60 (s, 1H), 8.16 (t, 1H, Im, 3JHH=1.8Hz), 7.88 (t, 1H, py, 3JHH=8.0Hz), 7.46 (t, 1H, Im, 3JHH=1.8Hz), 7.93 (d, 1H, py, 3JHH=8.1Hz), 6.86 (d, 1H, py, 3JHH=8.1Hz), 4.67 (q, 2H, CH2CH3, 3JHH=7.4Hz), 1.73 (t, 3H, CH2CH3, 3JHH=7.4Hz), 4.03 (s, 3H, OCH3). 13C NMR (125.76MHz, CDCl3, ppm): delta 164.26 (py), 144.11 (py), 142.64 (py), 135.10 (im), 123.12 (im), 119.50 (im), 112.35 (py), 106.58 (py), 54.91 (OMe), 46.51 (NCH2CH3 of cationic imidazolium), 16.25 (NCH2CH3 of cationic imidazolium). EI-MS (EI+): m/z 176.1 (Im-pyOMe)+.

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, 116241-61-3, 2-Fluoro-6-methoxypyridine.

Reference:
Article; Gerlach, Deidra L.; Siek, Sopheavy; Burks, Dalton B.; Tesh, Jamie M.; Thompson, Courtney R.; Vasquez, Robert M.; White, Nicholas J.; Zeller, Matthias; Grotjahn, Douglas B.; Papish, Elizabeth T.; Inorganica Chimica Acta; vol. 466; (2017); p. 442 – 450;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56946-65-7 ,Some common heterocyclic compound, 56946-65-7, molecular formula is C8H7Cl2N, 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 250-mL round bottomed flask was charged with 2,4-dichloro-6,7-dihydro-5H- cyclopenta[Z?]pyridine (1.05 g, 5.58 mmol), 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)cyclopent-2-enone (1.27 g, 6.14 mmol), tetrakis(triphenylphosphine)palladium(0) (0.322 g, 0.28 mmol), and Cs2C03 (5.45 g, 16.7 mmol). Toluene (30 ml), EtOH (7.5 ml) and water (15 ml) were added. The resulting mixture was stirred under argon at 90 C for 18 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (150 mL), hexanes (50 mL) and water (25 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 100 mL). The combined organic extract was washed with saturated sodium chloride (2 x 20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica using hexane/ethyl acetate (10:0 to 0: 10) as eluent to afford the title compound (0.305 g, 23%) as a yellow solid. MW = 233.69. ]H NMR (CDC13, 500 MHz) delta 7.41 (s, 1H), 6.79 (t, 7 = 2.0 Hz, 1H), 3.13 (t, 7 = 7.5 Hz, 2H), 3.10-3.06 (m, 2H), 3.04 (t, 7 = 7.5 Hz, 2H), 2.62-2.58 (m, 2H), 2.20 (quin, 7 = 7.5 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56946-65-7, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic 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, 64951-08-2, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of carboxylic acid (1.1 g, 7 mmol) in dry DCM (10 mL) at 0C under nitrogen was added B (1.5 mg, 7 mmol), Et3N (2.1 g, 21 mmol), EDCI (4.7 g, 23.8 mmol), HOBt (2.8 g, 21 mmol) and DMAP (150 mg, catalytic). Reaction mixture was stirred at 25C for 2-12 h, monitored by TLC. Mixture was poured into cold water (10 ml) and extracted with DCM (20ml), washed with water and brine, then dried and concentrated. Crude material was purified by column chromatography (silica gel, EtOAc_PE=l :2) to give C (751 mg, 30%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH; THE SCRIPPS RESEARCH INSTITUTE; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; CHATTERJEE, Arnab, K.; WANG, Feng; SCHULTZ, Peter, G.; XU, Chunping; AJAYI, Kehinde; WANG, Jianing; HALDER, Rajkumar; KUMAR, Puneet; YANG, Baiyuan; LIU, Renhe; CHENG, Bo; KANEKO, Takushi; WO2014/190199; (2014); 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. 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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. Formula: C6H4ClF3N2

6. l-(5-Amino-3-trifluoromethyl-pyridin-2~yl)-ethanone Heat a mixture of 6-chloro-5-trifluoromethyl-pyridin-3-ylamine (985 mg, 5.0 mmol), palladium acetate (20 mg), DPPP (60 mg), butyl vinyl ether (1.5 g, 15 mmol) and NaHCO3 (840 mg, 10 mmol) EPO in MeOH (10 mL) at 13O0C for 18 hours. Cool, filter and wash the solid with MeOH. Add 6M hydrochloric acid (5 mL), stir for 1 hour and evaporate the volatiles. Dissolve the residue in EtOAc (50 mL) and wash with saturated NaHCO3(aq) (50 mL) and brine (50 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure to yield the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 99368-68-0.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/42289; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 36357-38-7, Adding some certain compound to certain chemical reactions, such as: 36357-38-7, name is 5-Acetyl-2-methylpyridine,molecular formula is C8H9NO, 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 36357-38-7.

Sodium borohydride (2.3 g, 0.06 mol) was added in small portions over 30 min, to a solution of compound 2a (16.4 g, 0.121 mol) in ethanol (160 mL) at 0C and the reaction mixture was stirred at same temperature. After 1 h, the reaction mixture was diluted with sodium bicarbonate solution (sat) (2×200 mL) and extracted with dichloromethane (2×500 mL). The combined organic extract was dried over anhydrous sodium sulphate and concentrated to afford a pale yellow oil, which was purified by flash column chromatography (5% methanol/dichloromethane) to afford compound 3a (17.0 g; 93% yield over 2 steps) as a pale yellow oil. ES-MS [M+l]+: 138.1. 1H NMR (400 MHz, CDC13): delta 8.35 (d, J = 2.0 Hz, 1H), 7.63 (dd, J = 8.0, 2.4 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (br s, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H).

According to the analysis of related databases, 36357-38-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MINORYX THERAPEUTICS S.L.; GARCIA COLLAZO, Ana Maria; TEN HOEVE, Wolter; KOEK, Johannes Nicolaas; REWINKEL, Johannes B.M.; DE WILDE, Sander; (83 pag.)WO2018/116281; (2018); 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. 65753-52-8, name is 2-Fluoro-3-(trifluoromethyl)pyridine, molecular formula is C6H3F4N, 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-Fluoro-3-(trifluoromethyl)pyridine

750 g of 2-fluoro-3-trifluoromethylpyridine was added to the ammoniation reactor.700g of water was added to the ammoniation reactor, and then 250g of liquid ammonia was fed to the ammoniation reactor.Raise temperature to 130C, pressure not more than 3.0MPa, react for 10 hours,Cool down to 90 C, discharge to the receiving kettle, receive cooling down to 10 C,2-Amino-3-trifluoromethylpyridine is obtained by centrifugation and drying; the yield is about 95%

With the rapid development of chemical substances, we look forward to future research findings about 65753-52-8.

Reference:
Patent; Shandong Huimeng Biological Technology Co., Ltd.; Xiao Caigen; Liu Shuwen; (6 pag.)CN108003093; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19842-08-1 ,Some common heterocyclic compound, 19842-08-1, molecular formula is C7H8BrN, 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.

In a 2 L round-bottomed flask was charged n-butyllithium 2.5M hexanes (99 ml, 248 mmol) in Et2O (1680 ml) to give a colorless solution. The reaction was cooled to -78 C. n-Butyllithium 2.5M hexanes (99 ml, 248 mmol) was added dropwise keeping the temperature below -70 C. The reaction was stirred for 1 hour and N,N-dimethylformamide (36.6 ml, 473 mmol) was added keeping the temperature below -70 C. The reaction was stirred for 1 hour and quenched with saturated ammonium chloride solution (2 L). The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography eluting with 0-30% ethyl acetate to give 6-bromonicotinaldehyde. Yield 19.7 g, 44.8%In a 2 L round-bottomed flask was added Methyltriphenylphosphonium bromide (42.9 g, 120 mmol) in THF (600 ml) and cooled to -20 C. n-Butyllithium 2.5M hexanes (48.0 ml, 120 mmol) was added dropwise keeping the temperature below 0 C. The reaction was warmed to room temperature for 20 minutes and cooled back to 0 C. A solution of 6-bromonicotinaldehyde (18.6 g, 100 mmol) in THF (40 mL) was added. The reaction was warmed to room temperature and stirred overnight. The reaction was partitioned between water and diethyl ether (1 L) and the organic layer was dried over sodium sulfate, filtered and solvent removed at room temperature under reduced pressure. The product, 2-bromo-5-vinylpyridine, was purified by bulb to bulb distillation (600 mTorr, 80-100 C.). Yield 17.2 g, 93%2-Bromo-5-vinylpyridine (17.2 g, 40.1 mmol) was dissolved in ethanol (150 mL) and Adam’s Catalyst (PtO2, 75%, 1.4 g) was added. The mixture was hydrogenated at 3 psi of hydrogen, continually checking the progress of the reaction by LC and 1H NMR between each charge of hydrogen. After 10 psi was consumed, the data showed completion of the reaction with <5% of reduction of the bromine. The catalyst was filtered off and the solvent was removed under reduced pressure at 20 C. to give 2-bromo-5-ethylpyridine. Yield 17 g, 98%.In a 1 L round-bottomed flask was compound 6 (10 g, 53.8 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (13.83 g, 59.1 mmol) in Dioxane (300 ml) followed by saturated sodium bicarbonate (150 ml). The mixture was degassed by passing a stream of nitrogen through the mixture for 20 minutes. Tetrakis(triphenylphosphine) palladium(0) (3.36 g, 2.91 mmol) was added and the mixture was heated to reflux becoming very thick then finally going to solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure. The residue was purified by column chromatography 0-100% ethyl acetate/heptane to give 3-(5-ethylpyridin-2-yl)-4-methylaniline. Yield 8.7 g, 77%The urea was formed from 3-(5-ethylpyridin-2-yl)-4-methylaniline and 4-(2-amino-5-tert-butylthiophene-3-carbonyl)-3,3-dimethylpiperazine-2-one. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19842-08-1, its application will become more common. Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem