Pyridine-derivatives

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. 873107-98-3, name is 5-Iodo-2-(trifluoromethyl)pyridine, molecular formula is C6H3F3IN, 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. Application In Synthesis of 5-Iodo-2-(trifluoromethyl)pyridine

Step 2: ethyl 2,2-difluoro-2-(6-(trifluoromethyl)pyridin-3-yl)acetate [0252] To a solution of 5-iodo-2-(trifluoromethyl)pyridine (14.5 g, 53.2 mmol) and ethyl 2- bromo-2,2-difluoroacetate (10.8 g, 53.2 mmol) in DMF (250mL) was added Cu powder (6.76g, 106.4mmol). The mixture was heated to 80C for 20 hours. After 20 hours, the reaction mixture was poured into a solution of dibasic potassium hydrogen phosphate, trihydrate (121 g, 532 mmol) in water (1500 mL) with vigorous stirring. The suspension was filtered and the solid was rinsed with ether. The filtrate was added to brine and extracted with ether (2x). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The concentrate was purified by column chromatography over silica gel (hexane/EtOAc=50: l) to afford the title compound as a colorless liquid (8.96g, 63%). MS (ESI) calcd for CioH8F5N02: 269.2; found: 270.3 [M+H]. 1H NMR (400 MHz, CDCls) delta 8.98 (s, 1H), 8.14 (d, J= 8.2 Hz, 1H), 7.81 (d, J= 8.2 Hz, 1H), 4.35 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 873107-98-3.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (119 pag.)WO2015/187845; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 45644-21-1, name is 2-Amino-6-chloropyridine. A new synthetic method of this compound is introduced below., Safety of 2-Amino-6-chloropyridine

To a solution of 2-amino-6-chloropyridine (10.7 g, 83.5 mmol) in toluene (103 mL) NaHCO3 (14 g, 167 mmol) and pivaloyl chloride (15.4 mL, 125.2 mmol) were added at 0C. The resulting mixture was stirred at room temperature for 5 hours then the suspension was filtered and the solid was washed with DCM. The filtrates were concentrated undervacuum then heptane (22 mL) was added and the resulting mixture was concentrated. The solid was filtered, washed with heptane (15 mL) and dried under vacuum to afford the title intermediate (15.4 g, 72.4 mmol, 87% yield). LC-MS (M-H) = 213.2

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, 45644-21-1, 2-Amino-6-chloropyridine.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); 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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Chloro-4-iodopyridine

Method 2: Sonogashira route B Step 1 : 2-Chloro-4-phenylethvnyl-pyridine To the degassed mixture of triethylamine (375ml_) and acetonitrile (125ml_) was added 2-Chloro 4-iodopyridine (75g, 0.313mol), bis(triphenylphosphine) palladium(ll)chloride (4.4g, 2mol%) and copper iodide (0.6g, 1 mol%) sequentially. The mixture was stirred at room temperature for 3h. Phenylacetylene dissolved in acetonitrile(250 ml_) was then added dropwise to reaction mixture and it was stirred for 1 hr at room temperature. Reaction was monitored by TLC. Acetonitrile and triethylamine was removed under vacuo, and the residue was purified by column chromatography using silica with mixture of ethyl acetate and hexane solvent system to yield product (59g, 88%).1 H NMR (CDCIa): delta 8.36( d, J = 5.2 Hz, 1 H), 7.53-7.55 (m, 2H), 7.43( s, 1 H), 7.39- 7.42(m, 3H), 7.29(dd, J = 5.4 Hz, 1.2 Hz, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CEDERBAUM, Fredrik; UMARYE, Jayant; DUMEUNIER, Raphael; SONAWANE, Ravindra; WO2012/84678; (2012); 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. 85331-33-5, name is 3,5-Dichloropicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H2Cl2N2

3,5-Dichloro-pyridine-2-carbonitrile (10 g, 57 8 mmol) was dissolved in 100 mL of 95% concentrated sulfuric acid and this mixture was heated to 115 C overnight The reaction mixture was then cooled, poured over ice with strong stirring The resulting solid was filtered, washed with water and dried at 40 C under reduced pressure to give 94g (85%) of pure product as a white 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, 85331-33-5, 3,5-Dichloropicolinonitrile.

Reference:
Patent; ARDEA BIOSCIENCES INC.; WO2009/89263; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19524-06-2, 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 19524-06-2, name is 4-Bromopyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

4-Bromopyridine hydrochloride (11.7 g) and 4-carboxyphenylboronic acid (10.0 g) were dissolved in a solvent mixture of toluene (250 mL) and water (250 mL), and to the solution were sequentially added tetrakis(triphenylphosphine)palladium(0) (5.0 g) and anhydrous sodium carbonate (25.4 g), followed by heating under reflux at 120°C for 19 hours. After the resultant mixture was cooled to room temperature, ethyl acetate was added thereto, and the thus-obtained mixture was extracted with water. Concentrated HCl was added to the aqueous layer, to thereby make the mixture acidic. The aqueous layer was washed with ethyl acetate, and was concentrated. The resultant solid was collected by filtration, to thereby give the title compound (8.37 g).1H-NMR(DMSO-d6) delta:8.11(2H, d, J=8.8Hz), 8.14(2H, dJ=8.8Hz), 8.35(2H, d, J=6.6Hz), 8.97(2H, d, J=6.6Hz). MS (FAB) m/z:200 (M+H)+.

According to the analysis of related databases, 19524-06-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1577301; (2005); 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. 59782-87-5, name is 6-Chloro-5-iodonicotinic acid, molecular formula is C6H3ClINO2, 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. category: pyridine-derivatives

DMF (1.927 mL, 24.89 mmol) and SOCl2 (18.17 mL, 249 mmol) were added to a suspension of 6-chloro-5-iodo-3-pyridinecarboxylic acid (24 g, 83 mmol) in toluene (165 mL)and the RM was stirred at 80C for 1 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in THF (165 mL). DIPEA (29.0 mL, 166 mmol) was added and the mixture was cooled down to -15C, treated dropwise with a solution of 4- (trifluoromethoxy)aniline (15.43 g, 87 mmol) in THF (165 mL) and was stirred at RT for 1 h. The solvent was off under reduced pressure and the residue was dissolved in TBME (500 mL), washed with IN HCl, a sat. aq. solution of NaHC03 and brine, dried over Na2S04 and the solvent was evaporated off under reduced pressure and the product was recrystallized from EtOAc / n- heptane to afford the title compound as a white solid. UPLC-MS (Condition 2) tR = 1.23 min, m/z = 440.8 [M-H]

With the rapid development of chemical substances, we look forward to future research findings about 59782-87-5.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); 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. 1072-97-5, name is 5-Bromopyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromopyridin-2-amine

a) 5-Cyclopropyl-pyridin-2-ylamine; To a solution of 5-bromo-pyridin-2-ylamine (2 g, 11.55 mmol) and cyclopropyl boronic acid (2.98 g, 34.68 mmol) in toluene (40 mL) and water (2 mL) was added K3PO4 (8.59 g, 40.46 mmol) under an argon atmosphere. A balloon containing argon was affixed, and the reaction flask was purged to ensure a argon atmosphere. To this were added Pd(OAc)2, (259.52 mg, 1.16 mmol) and tricyclohexylphosphene (647.3 mg, 2.3 mmol) and stirred at 80 C. for 16 h. The reaction mixture was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.1 g, 71%).1H NMR (DMSO, 400 MHz): delta(ppm)=7.73 (s, 1H), 7.04-7.02 (dd, J=8.48 & 2.04 Hz, 1H), 6.34 (d, J=8.48 & 2.04 Hz, 1H), 5.60 (s, 2H), 1.78-1.66 (m, 1H), 0.822-0.77 (m, 2H), 0.52-0.313 (m, 2H)

The synthetic route of 1072-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baumann, Karlheinz; Goetschi, Erwin; Green, Luke; Jolidon, Synese; Knust, Henner; Limberg, Anja; Luebbers, Thomas; Thomas, Andrew; US2011/190269; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 884494-81-9, name is 3-Bromo-5-fluoro-2-methoxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-5-fluoro-2-methoxypyridine

To a solution of 5.0 g (24 mmol) 3-bromo-5-fluoro-2-methoxypyridine in 200 mL of toluene were added 5.2 g (31 mmol) of methyl pyrrolidine-2-carboxylate hydrochloride, 3.0 g (4.9 mmol) of BINAP, 31 .6 g (97.0 mmol) of Cs2C03and 2.5 g (2.4 mmol) of Pd2(dba)3CHCI3. The mixture was stirred at 90 C overnight under nitrogen atmosphere. It was diluted with 200 mL of ethyl acetate, washed with three 50 mL portions of water, and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure to afford a residue, which was purified by chromatography on silica gel column eluting with 18 % of ethyl acetate in petroleum ether to afford compound 16-1 . LC-MS: m/e = 255 [M+H]+.

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, 884494-81-9, 3-Bromo-5-fluoro-2-methoxypyridine.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 871836-51-0, 4-Chloro-1H-pyrazolo[4,3-c]pyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Preparation P3 4-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (P3) p-Toluenesulfonic acid monohydrate (2.4 g, 13 mmol) and 3,4-dihydro-2H-pyran (99percent, 45 mL, 520 mmol) were sequentially added to a suspension of 4-chloro-1H-pyrazolo[4,3-c]pyridine (20.0 g, 130 mmol) in dichloromethane (400 mL). The reaction mixture was allowed to stir at room temperature for 24 hours, at which time it was washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Eluents: 10percent, then 30percent, then 50percent ethyl acetate in heptane) afforded the product as a white solid. Yield: 27.51 g, 115.7 mmol, 89percent. LCMS m/z 238.1 [M+H+]. 1H NMR (400 MHz, CDCl3) delta 8.19 (d, J=6.0 Hz, 1H), 8.16 (d, J=0.9 Hz, 1H), 7.47 (dd, J=6.0, 0.9 Hz, 1H), 5.73 (br dd, J=9.0, 2.7 Hz, 1H), 3.97-4.04 (m, 1H), 3.72-3.80 (m, 1H), 2.43-2.53 (m, 1H), 2.07-2.20 (m, 2H), 1.65-1.85 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,871836-51-0, 4-Chloro-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6188-25-6, Adding some certain compound to certain chemical reactions, such as: 6188-25-6, name is 6-Chloroimidazo[1,2-a]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 6188-25-6.

To 6-chloro-imidazo[1,2-a]pyridine (1 eq, 253 mmol, 39 g) in acetic acid (500 ml) under inert atmosphere, is added dropwise bromine (1 eq, 253 mmol, 13 ml). After 1 hour stirring at room temperature, the reaction mixture is filtered and to give a beige solid (64 g) 3-Bromo-6-chloro-imidazo[1,2-a]pyridine hydrobromide;[M+H]+ 232(234)

According to the analysis of related databases, 6188-25-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2009/50183; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem