Day: July 6, 2021

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. 101079-63-4, name is 2,6-Dichloropyridine-3,4-diamine. A new synthetic method of this compound is introduced below., name: 2,6-Dichloropyridine-3,4-diamine

To a solution of intermediate 13 (16.00 g, 89.88 mmol) in EtOH (60 mL) was added triethyl orthoacetate (50 mL) and conc. HCl (4 mL) and the mixture was stirred at 100 C for 16 hours. The mixture was concentrated and diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by column chromatography over silica gel (mobile phase gradient: from 100% petrol, 0% EtOAc to 0% petrol, 100% EtOAc). The product containing fractions were collected and the solvent was evaporated to give 11 g of intermediate 14 (57% yield, yellow solid).

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, 101079-63-4, 2,6-Dichloropyridine-3,4-diamine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; PILATTE, Isabelle, Noelle, Constance; QUEROLLE, Olivier, Alexis, Georges; ANGIBAUD, Patrick, Rene; BERTHELOT, Didier, Jean-Claude; COUPA, Sophie; DEMESTRE, Christophe, Gabriel, Marcel; MEERPOEL, Lieven; MERCEY, Guillaume, Jean, Maurice; MEVELLEC, Laurence, Anne; MEYER, Christophe; PASQUIER, Elisabeth, Therese, Jeanne; PONCELET, Virginie, Sophie; (104 pag.)WO2017/216293; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65156-94-7, Adding some certain compound to certain chemical reactions, such as: 65156-94-7, name is 5-Chloro-1H-pyrrolo[3,2-b]pyridine,molecular formula is C7H5ClN2, 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 65156-94-7.

A mixture of 5-chloro-lH-pyrrolo[3,2-b]pyridine (1 g, 6.55 mmol, 1 equiv), 1,1,1- trifluoro-2-iodoethane (1.4 g, 6.55 mmol, 1 equiv) and CS2CO3 (2.1 g, 6.55 mmol, 1 equiv) in 10 mL of DMF was stirred for 4 hours at 60 C. The reaction was then quenched by the addition of 30 mL of water, extracted with 10 mL of ethyl acetate and the combined organic layers concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petr oleum ether (1/10) to afford the desired final product as a colorless oil in 42% yield.

According to the analysis of related databases, 65156-94-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 874959-68-9 , The common heterocyclic compound, 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride, molecular formula is C5H3BrClNO2S, 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.

Example 58(a) l-(5-Bromo-pyridine-2-sulfonyl)-4-methyl-piperazine; 5-Bromopyridine-2-sulfonyl chloride (as described in Example 52(b) (55.0 mg, 0.214 mmol) was dissolved in CH2Cl2 (1 mL) and 1-methyl-piperazine (26 muL, 0.236 mmol) was added. Stirring was continued at room temperature for 3 hours and saturated aqueous NaHCO3 (1 mL) was added. The mixture was diluted with CH2Cl2 (5 mL) and the aqueous phase was extracted with CH2Cl2 (3 x 5 mL). The combined organic phases were dried (Na2SO4) and concentrated to afford the title compound (61 mg, 89%). 1H NMR (400 MHz, CDCl3) delta ppm 2.29 (s, 3 H) 2.33 – 2.38 (m, 2 H) 2.45 – 2.50 (m, 2 H) 3.10 – 3.18 (m, 2 H) 3.30 – 3.37 (m, 2 H) 7.31 (d, J=4.29 Hz, 1 H) 7.81 (d, J=7.58 Hz, 1 H) 8.04 (dd, J=8.34, 2.27 Hz, 1 H); MS (ESI) m/z 321 (M + 1).

The synthetic route of 874959-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/2244; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1122-71-0, 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.1122-71-0, name is 6-Methyl-2-pyridinemethanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.

A solution of 0.45 g (3.65 mmol, 1.0 eq.) of of (6-methylpyridin-2-yl)methanol in 8 mL of anhydrous acetonitrile was added to a rapidly stirred mixture of 0.89 g mmol (5.48 mmol, 1.5 eq.) of 1,1?-carbonyldiimidazole in 1.5 mL of anhydrous acetonitrile. The reaction mixture was stirred for 40 minutes, and the volatiles were then removed in vacuo. The residue was redissolved in 30 mL of ethyl acetate and washed with 30 mL of water. The layers wereseparated and the organic phase was washed with 2 x 20 mL of sat. sodium bicarbonate solution, followed by 20 mL of brine. The organic phase was dried (Na2SO4), filtered and evaporated to dryness. The residue was dried under high vacuum to provide 0.65 g (3.0 mmol, 82%) of (6-methylpyridin-2-yl)methyl imidazole-1-carboxylate (0.65g, 82% yield). ?H NMR (300 MHz, CDC13) oe: 8.20 (t, 1H), 7.65 (t, 1H), 7.50-7.45 (m, 1H), 7.23 (d, 1H), 7.17(d, 1H), 7.09 (m, 1H), 5.49 (s, 2H), 2.59 (s, 3H).

Statistics shows that 1122-71-0 is playing an increasingly important role. we look forward to future research findings about 6-Methyl-2-pyridinemethanol.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; COLE, Andrew G.; KULTGEN, Steven; (203 pag.)WO2018/52967; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6959-48-4, 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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

Reference Example 22 N-(4-Bromophenyl)-N-((pyridin-3-yl)methyl)pyrimidin-2-amine [Show Image] Under an argon atmosphere, N-(4-bromophenyl)pyrimidin-2-amine (200 mg) was added to a suspension of sodium hydride (48 mg) in anhydrous DMF (8 ml), and the resulting mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0C, and 3-chloromethylpyridine hydrochloride (600 mg) and triethylamine (1.00 ml) were added thereto, followed by stirring the resulting mixture at room temperature for 2 hours. Saturated brine was added to the reaction solution and the resulting mixture was extracted 3 times with ethyl acetate. Organic layers were washed 3 times with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: ethyl acetate/hexane = 3/1) to obtain N-(4-bromophenyl)-N-((pyridin-3-yl)methyl)pyrimidin-2-amine (232 mg). NMR(H1, CDCl3):delta 5.23(2H, s), 6.65(1H, t, J=4.6Hz), 7.08-7.12(2H, m), 7.20(1H, dd, J=7.8, 4.9Hz), 7.46-7.50(2H, m), 7.59-7.61(1H, m), 8.35(2H, d, J=4.6Hz), 8.49(1H, dd, J=4.9, 1.5Hz), 8.54(1H, d, J=2.2Hz)

According to the analysis of related databases, 6959-48-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toray Industries, Inc.; EP2033637; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69950-65-8, 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. 69950-65-8, name is Methyl 6-formyl-2-pyridinecarboxylate. A new synthetic method of this compound is introduced below.

[00232] N-BOC-N?-((6-methylpicol-2-yI)methyl)-trans-1 ,2- diaminocyclohexane (3). A batch of 349 mg (1 .63 mmol) N-BOO-trans-i ,2-diaminocyclohexane (1)14 was added to 269 mg (i .63 mmol) of methyl 6- formylpyridine-2-carboxylate (2)15 stirring in iO mL MeOH. Small aliquots of this reaction were removed and concentrated to dryness for NMR analysis to confirm full Schiff base formation. After 2 hours, the reaction was cooled to 000 and 66 mg (i .75 mmoL) NaBH4 was added in i mL MeOH forming a deep red solution within minutes.After 2 hours of stirring at 0C, the reaction was quenched with satd. NaHCO3(aq) and MeOH was removed via rotary evaporation. The volume of the resultant solution was doubled via addition of 0H2012 and the reaction was brought to pH 7 using i M HCI(aq). The organic layer was separated the aqueous phase washed 3x with 0H2012. The 0H2012 was pooled, dried over Na2504 and concentrated to 502 mg (i .38 mmol,85 %) of 3 as a yellow oil. 1H NMR (ODd3, 400 MHz), 6 (ppm): 7.97 (d, i H), 7.75 (t,iH), 7.54 (d, br, iH), 5.i8 (d, br, iH, NH), 4.08 (d, iH), 3.99-3.95 (m, 4H), 3.32 (m, br, i H), 2.37 (m, i H), 2.09-2.Oi (m, 2H), i .66-i .62 (m, 2H), i .4i (5, 9H), i .29-i .05 (m, 4H). 130 NMR (ODd3, iOO MHz), 6 (ppm): i65.95, i6i.82, i56.2i, i47.24, i37.33, i25.70, i23.35, 79.07, 64.67, 60.42, 54.75, 5i.28, 33.i8, 3i.97, 28.49,24.97, 24.6i. ESI (M + H) m/z = 364.3; calcd: 364.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69950-65-8, its application will become more common.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; CARAVAN, Peter; BOROS, Eszter; GALE, Eric, M.; WO2014/75079; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 94015-05-1, name is 4-Methylnicotinic acid hydrochloride, the common compound, a new synthetic route is introduced below. Quality Control of 4-Methylnicotinic acid hydrochloride

To a solution of 4-methyl nicotinic acid hydrochloride (0.40 g, 2.30 mmol, 1 eq) in DMF dry (4.0 mL), ammonium chloride (0.74 g, 13.90 mmol, 6 eq), HOBt (0.45 g, 3.30 mmol, 1.44 eq), EDCI (0.64 g, 3.30 mmol, 1.44 eq) and N-methylmorpholine (0.63 mL, 5.60 mmol, 2.44 eq) were subsequently added. The reaction was stirred at room temperature, under nitrogen for 3 h. Evaporation of the solvent gave a residue which was purified by column chromatography (neutral alumine oxide, Brockmann grade III) using EtOAc as eluant to give 6 as white solid after crystallization with EtOAc (0.25 g, 79%). Mp. 157-162 C. 1H NMR (300 MHz, CD3OD) delta 8.52 (s, 1-H), 8.43 (d, J = 5.2 Hz, 1-H), 7.34 (d, J = 5.2 Hz, 1-H), 2.49 (s, 3-H); 13C NMR (75 MHz, CD3OD) delta 170.8, 149.6, 146.8, 146.7, 132.9, 126.1, 18.2; GC-MS m/z 136 (M)+; IR (KBr) 3335, 3046, 2800, 1685, 1597, 1430, 1175, 842 cm-1. Anal. Calcd for C7H8N2O: C, 61.75; H, 5.92; N, 20.58. Found: C, 62.10; H, 6.25; N, 20.60.

The synthetic route of 94015-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Galli, Ubaldina; Mesenzani, Ornella; Coppo, Camilla; Sorba, Giovanni; Canonico, Pier Luigi; Tron, Gian Cesare; Genazzani, Armando A.; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 58 – 66,9;,
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.18368-63-3, name is 2-Chloro-6-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.SDS of cas: 18368-63-3

2-Chloro-6-methylpyridine (1.6 g), 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidine (4.0 g), sodium t-butoxide (1.5 g), tris(dibenzylidenacetone)dipalladium (O)-chloroform adduct (0.2 g) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.25 g) were added to toluene (15 ml), and heated for 1 hour at 120C using a microwave reactor (trade name: INITIATOR, manufactured by Biotage). Upon the completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the precipitate was filtered off through a short silica gel layer. The filtrate was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2-methyl-6-[3-(3,4,5-trichlorophenyl)-3- (trifluoromethyl)pyrrolidin-l-yl]pyridine (3.4 g).1H-NMR: see the table below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-63-3, 2-Chloro-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; MIHARA, Jun; HATAZAWA, Mamoru; YAMAZAKI, Daiei; KISHIKAWA, Hidetoshi; DOMON, Kei; WATANABE, Hidekazu; SASAKI, Norio; MURATA, Tetsuya; ARAKI, Koichi; SHIMOJO, Eiichi; ICHIHARA, Teruyuki; ISHIKAWA, Tadashi; SHIBUYA, Katsuhiko; GOeRGENS, Ulrich; BRUeCHNER, Peter; FISCHER, Reiner; JANSEN, Johannes-Rudolf; KAPFERER, Tobias; MAECHLING, Simon; MAUE, Michael; VOERSTE, Arnd; WO2012/35011; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53052-06-5 ,Some common heterocyclic compound, 53052-06-5, molecular formula is C6H4N2OS, 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.

2-(Mbetathv)thio)ri,31oxazolor4,5-biPyridine; A 250 mL RB flask, equipped with a magnetic stirring bar and nitrogen gas inlet, was charged with [1,3]oxazolo[4,5-b]pyridine-2(3H)-thione (5.00 g, 32.9 mmol), potassium carbonate (4.54 g, 32.8 mmol), and 80 mL of anhydrous DMF. Then iodomethane (2.45 mL, 5.57 g, 39.3 mmol) was added dropwise to the stirring reaction mixture under nitrogen. The mixture was stirring for 2 h, then diluted with 300 mL of water, and extracted with EtOAc (4×150 mL). The combined organic extract was washed with water (3×100 mL), then with brine (100 mL), dried over Na2SO4 and evaporated to give 4.53 g (83 %) of 2- (methylthio)[1,3]oxazolo[4,5-b]pyridine as a tan solid. LCMS m/z (M+H): 167.1. 1H NMR (300 MHz, DMSO-d6): delta 8.44 (1H), 8.08 (1H), 7.35 (1H), 2.81 (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. 53052-06-5, Oxazolo[4,5-b]pyridine-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2006/51410; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137640-84-7, 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. 137640-84-7, name is 6-(3-(Trifluoromethyl)phenoxy)picolinic acid. A new synthetic method of this compound is introduced below.

EXAMPLE 24 Preparation of N-(2,4-difluorophenyl)-2-(3-alpha,alpha,alpha-trifluoromethylphenoxy)-6-pyridinecarboxamide 6-(3-alpha,alpha,alpha-Trifluoromethylphenoxy)picolinic acid (7.1 g) in thionyl chloride (50 ml) was refluxed for 1 hour. The excess thionyl chloride was evaporated in vacuo and dichloromethane added to the residual picolinoyl chloride. A solution of 2,4-difluoroaniline (3.3 g) and triethylamine (2.6 g) in dichloromethane (50 ml) was then added dropwise with stirring at ambient temperature. After stirring a further 1 hour, the reaction mixture was washed with water, dried over anhydrous magnesium sulphate and the dichloromethane evaporated. The residue was purified on a silica gel column using dichloromethane as eluant to give the title compound (6.9 g) as a white solid of melting point 110-111 C. m/e Theory: Found 394:394

At the same time, in my other blogs, there are other synthetic methods of this type of compound,137640-84-7, 6-(3-(Trifluoromethyl)phenoxy)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Shell Research Limited; US5294597; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem