Pyridine-derivatives

Synthetic Route of 14338-32-0, 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. 14338-32-0, name is 2-Chloro-1-methylpyridinium iodide, molecular formula is C6H7ClIN, 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.

Step F: 2-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amide To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3*30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2*50 cm3), brine (1*50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluding with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H) +522.3.

According to the analysis of related databases, 14338-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dolle, Roland E.; Tuthill, Paul Anson; US2004/209857; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5409-39-2, 5-Chloro-3-nitropyridin-2-amine, 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, 5409-39-2, blongs to pyridine-derivatives compound. Formula: C5H4ClN3O2

To a solution of intermediate 32a (10.0 g, 57.6 mmol) in HBr [(31 .0 mL (100%), 286.4 mmol)] at 0 00 sodium nitrite (13.8 g, 199.9 mmol) was added drop wise. To the stirred solution Br2 (10.0 mL, 197.1 mmol) was added in water and stirred at room temperature for 1 h. The reaction mixture was basified with NaHCO3 solution (pH=7) and extracted with ethyl acetate, washed with water, and dried over anhydrousNa2SO4 The solvent was removed under vacuo to yield the title product (10.0 g,73.0%) 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,5409-39-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58584-86-4 ,Some common heterocyclic compound, 58584-86-4, molecular formula is C8H7Cl2NO2, 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.

The first step of Scheme 5: A dry round bottom flask was charged with NaH (264 mg of a 60% dispersion in mineral oil, 6.6 mmole) and the reagent washed twice with hexane. 5 mL dry DMF was added and benzyl alcohol (0.62 mL, 6.0 mmole) was added dropwise. After H2 evolution had ceased the reaction mixture was added dropwise to a 0 C. solution (10 mL) of 2,6-dichloro-nicotinic acid ethyl ester (1.33 g, 6.0 mmole). It was stirred 15 minutes, and then allowed to stir another 20 minutes at room temperature. The reaction mixture was then poured into 150 mL water and extracted with ether (3×75 mL). Combined organic phases were washed with water, brine and dried over MgSO4. Filtration and evaporation gave the crude product which was then purified by chromatography on silica gel using a gradient of hexane/EtOAc (0 to 4%) as eluent. Pure fractions were combined and evaporated to give 818 mg (47%) of a 1:1 mixture of 2-benzyloxy-6-chloro-nicotinic acid ethyl ester and 6-benzyloxy-2-chloro-nicotinic acid ethyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-86-4, its application will become more common.

Reference:
Patent; Lee, Jinbo; Kirincich, Steve J.; Smith, Michael J.; Wilson, Douglas P.; Follows, Bruce C.; Wan, Zhao-Kui; Joseph-McCarthy, Diane M.; Erbe, David V.; Zhang, Yan-Ling; Xu, Weixin; Tam, Steve Y.; US2005/203081; (2005); 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. 82257-09-8, name is 3-Bromo-4-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A mixture of Compound 4 (150 mg, 414.11 mumol, 1 eq), 3-bromo-4-methoxy-pyridine (77.86 mg, 414.11 mumol, 1 eq), Pd(PPh3)2Cl2 (29.07 mg, 41.41 mumol, 0.1 eq), Na2CO3 (87.78 mg, 828.21 mumol, 2 eq) in dioxane/H2O (10 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 110 C. for 3 hr under N2 atmosphere. The reaction mixture was diluted with H2O (20 mL), then the mixture was extracted with EA (20 mL*3). The combined organic layers were washed with brine (20 mL*2), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Silica gel, Petroleum ether/Ethyl acetate=0:1). Then the residue was purified by prep-HPLC (column: Phenomenex Gemini 150*25 mm*10 um; mobile phase: [water (10 mM NH4HCO3)-ACN]; B %: 24%-54%, 10 min). Example 55 (23 mg, 63.63 mumol, 15% yield, 95% purity) was obtained as a light yellow solid. 1H NMR (400 MHz, CDCl3) delta=1.33-1.44 (m, 1H), 1.91-2.13 (m, 2H), 3.94 (s, 3H), 4.79-5.05 (m, 1H), 6.96 (d, J=5.87 Hz, 1H), 7.63 (dd, J=8.38, 1.65 Hz, 1H), 7.87 (d, J=8.44 Hz, 1H), 8.02 (d, J=1.47 Hz, 1H), 8.51-8.55 (m, 2H), 10.35 (br s, 1H); LCMS (electrospray) m/z 344.3 (M+H)+.

The synthetic route of 82257-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 1ST Biotherapeutics, Inc.; LEE, Jinhwa; KIM, Jae Eun; JO, Suyeon; LEE, Gwibin; LIM, Keonseung; PARK, A Yeong; KIM, Misoon; JUNG, Gyooseung; LIM, Seung Mook; LEE, Minwoo; YANG, Heekyoung; KIM, Hyonam; KIM, Hyeongjun; LI, Wanjun; FAN, Mingzhu; (82 pag.)US2019/100500; (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. 52568-28-2, name is 2-(Pyridin-2-yl)propan-2-amine, molecular formula is C8H12N2, 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. Recommanded Product: 2-(Pyridin-2-yl)propan-2-amine

General procedure: To a solution of the acid (1 equiv.) in DCM (0.2 M) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.), DIPEA (1.2 equiv.) at 0 C. After the mixture was stirred for 10 min, the amine (1.2 equiv.) was added. The reaction was stirred overnight at room temperature. Then water was added and the mixture was extracted with DCM. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography on silica gel to give the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 52568-28-2.

Reference:
Article; Wang, Haifeng; Niu, Youhong; Zhang, Guoying; Ye, Xin-Shan; Tetrahedron Letters; vol. 57; 41; (2016); p. 4544 – 4548;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1000522-43-9, Adding some certain compound to certain chemical reactions, such as: 1000522-43-9, name is 2-(5-Chloropyridin-2-yl)acetic acid,molecular formula is C7H6ClNO2, 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 1000522-43-9.

4-Cyclopropyl-[1,2,3]triazol-1-yl)acetic acid (Preparation 121 , 85 mg, 0.508 mmol) and (4-Aminopyridin-2-yl)-(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (Preparation 29, 100 mg, 0.338 mmol) were dissolved in THF (5 mL), followed by the addition of Et3N (0.165 mL, 1 .18 mmol) and 1 -propylphosphonic acid cyclic anhydride (50% solution in EtOAc, 0.507 mL, 0.845 mmol) at room temperature. The resultant mixture was stirred at room temperature for 16 hours and then diluted with ethyl acetate (20 mL). The organic layer was washed with aqueous saturated NaHCO3 solution, water, brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude residue was purified using preparative TLC eluting with 3% MeOH in DCM to afford the title compound as brown solid in 25% yield, 37 mg. 1H NMR (400 MHz, DMSO-d6): delta ppm 0.72-0.73 (m, 2H), 0.90-0.93 (m, 2H), 1 .82 (s, 9H), 1 .95-1 .98 (m, 1 H), 5.29 (s, 2H), 7.82 (d, 1 H), 7.86 (s, 1 H), 8.23 (s, 1 H), 8.65 (d, 1 H), 8.97 (s, 1 H), 9.20 (s, 1 H), 9.59 (s, 1 H), 1 1 .16 (br, 1 H). LCMS Rt = 3.17 minutes MS m/z 445 [M+H]+. The following examples were prepared according to Method 2 (Example 36) followed by method 1 Step 2 using 4M HCI in dioxan, using (4-aminopyridin-2-yl){7-[(1 R)-1 -methyl- 2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (Preparation 22) or (4-aminopyridin-2-yl){7-[(1 S)-1 -methyl-2-(tetrahydro-2H-pyran-2- yloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (Preparation 23) and the appropriate acetic acids.

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. 1000522-43-9, 2-(5-Chloropyridin-2-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944317-53-7, 4-Methyl-5-nitro-2-(trifluoromethyl)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, COA of Formula: C7H5F3N2O2, blongs to pyridine-derivatives compound. COA of Formula: C7H5F3N2O2

Into a 1L 3-necked round-bottom flask was placed 4-methyl-5-nitro-2- (trifluoromethyl)pyridine (60 g, 291.26 mmol, 1 equiv), Fe (48.9 g, 873.79 mmol, 3 equiv), NH4CI (77.2 g, 1456.31 mmol, 5 equiv), and H2O (500 mL). The resulting mixture was stirred for 2 at 80 C. The resulting solution was extracted with ethyl acetate. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/10) to give (27 g, 60.76%) of the title compound as a white solid. LC-MS: (ES, m/z): [M+H]+ 177.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944317-53-7, 4-Methyl-5-nitro-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary, Plake; DILLON, Michael, Patrick; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (248 pag.)WO2019/156987; (2019); A1;,
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 139585-70-9, name is 6-Bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinonitrile

lOld (59 mg, 0.19 mmol), 2-bromo-5-cyanopyridine (52 mg, 0.28 mmol), trans- dichlorobis(triphenylphosphine)palladium (II) (14 mg, 0.02 mmol), and copper(I) iodide (6 mg, 0.03 mmol) were mixed in a round bottom flask and placed under a nitrogen atmosphere. THF (1 mL) and triethylamine (0.053 mL, 0.380 mmol) were added, and the reaction mixture was stirred at 60 C for 1.5 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with sat’d aqueous NH4CI followed by brine, dried over MgSO/i, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0 to 50% EtOAc in heptane) gave 6-((3-((lS,5S,6S)-3-amino-l,5- bis(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4- fluorophenyl)ethynyl)nicotinonitrile (101, 33 mg, 0.08 mmol, 42% yield) as an off-white solid. LC/MS (ESI+) m/z = 413.1 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 9.05 (d, J = 1.37 Hz, 1H) 8.38 (dd, J = 8.22, 2.15 Hz, 1H) 7.96 (dd, J = 7.63, 2.15 Hz, lH) 7.85 (d, J = 8.22 Hz, 1H) 7.67 (ddd, J = 8.31, 4.50, 2.25 Hz, 1H) 7.35 (dd, J = 11.93, 8.41 Hz, 1H) 6.54 (s, 2H) 4.58 – 4.77 (m, 2H) 4.38 – 4.58 (m, 2H) 1.85 (t, J = 8.12 Hz, 1H) 1.19 (dd, J = 9.68, 5.38 Hz, 1H) 0.58 – 0.64 (m, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 139585-70-9.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 97483-77-7, 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 97483-77-7, name is 5-Bromopicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 Preparation of (5-Bromo-pyridin-2-ylmethyl)-carbamic acid tert-butyl ester To a solution of 5-Bromo-pyridine-2-carbonitrile (1.0 g, 5.46 mmol) in methanol (10 mL) at 0 C. is added NiCl2.6H2O (0.12 g, 0.54 mmol), Di-tert-butyl dicarbonate (2.38 g, 0.010 mmol) and NaBH4 (0.413 g, 0.010 mmol) at 0 C. then stirred at room temperature for 14 hours. The reaction solvent is removed under reduced pressure and crude is diluted with water and ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated in vacuum. The crude is purified by column chromatography eluting with 30% ethyl acetate in hexane to afford the title compound (650 mg). 1H-NMR (400 MHz, CDCl3) delta: 1.44 (s, 9H), 4.37 (d, J=5.44 Hz, 2H), 5.41 (bs, 1H), 7.18 (d, J=8.28 Hz, 1H), 7.75-7.78 (dd, J1=8.32 Hz, J2=2.28 Hz, 1H), 8.57 (d, J=2.08 Hz, 1H). LC-MS (m/z): [M+H]=289.0.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 97483-77-7, 5-Bromopicolinonitrile.

Reference:
Patent; Curtis, Michael; Duclos, Brian A.; Ewin, Richard A.; Johnson, Paul D.; Johnson, Timothy Allen; Vairagoundar, Rajendran; Billen, Denis; Goodwin, Richard M.; Haber-Stuk, Andrea K.; Kyne, Graham M.; Sheehan, Susan M. K.; US2013/237502; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 139585-70-9, 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 139585-70-9, name is 6-Bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Under an argon atmosphere, tert-butyl (2-{methyl[3-(2-piperazin-1-ylpyrimidin-5-yl)benzyl]amino}-2-oxoethyl)carbamate (200 mg) and 6-bromonicotinonitrile (124 mg) were dissolved in toluene (6 ml), and tris(dibenzylideneacetone) dipalladium (124 mg), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (169 mg), and cesium carbonate (222 mg) were added thereto, followed by stirring at 100 C. for 6 hours. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (0% to 7% MeOH/CHCl3) to obtain tert-butyl {2-[(3-{2-[4-(5-cyanopyridin-2-yl)piperazin-1-yl]pyrimidin-5-yl}benzyl)(methyl)amino]-2-oxoethyl}carbamate (122 mg).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 139585-70-9, 6-Bromonicotinonitrile.

Reference:
Patent; Astellas Pharma Inc.; US2012/184520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem