Pyridine-derivatives

Electric Literature of 98198-48-2, 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. 98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

Nitric acid (0.7 ml) was added dropwise to a solution of 5-bromo-4-methylpyridine-2-amine (2.0 g) in concentrated sulfuric acid (8.7 ml) at 55 C. over 30 minutes, and the mixture was stirred at the same temperature for 3 hours. After further stirring at room temperature for 2 hours, the reaction solution was poured into ice water. A 50% aqueous sodium hydroxide solution was added, and the resulting precipitate was collected by filtration, washed with distilled water and then dried under reduced pressure to give the title compound (2.5 g).MS (ESI) m/z: 268 (M+H)+.1H-NMR (CDCl3) delta: 2.54 (3H, s), 5.83 (2H, brs), 8.29 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98198-48-2, 2-Amino-5-bromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); 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. 93683-65-9, name is 6-Chloro-3-nitropicolinonitrile, molecular formula is C6H2ClN3O2, 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

Method A: To a solution of delta-chloro^-cyano-S-nitro-pyridine (3.03 g, 16.5 mmol) in ethanol (166 ml) and H2O (16 ml) was added iron (165 mmoi, 9.2 g) and calcium chloride (2.75 g, 24.8 mmol). The reaction mixture was refluxed for 4 hours and then cooled down to room temperature. The precipitate was filtered off over Celite and the filtrate was evaporated to dryness. The residue was redissolved in ethyl acetate and extracted with brine. The aqueous layer was extracted back with ethyl acetate. The combined organic layers were evaporated in vacuo. The residue was adsorbed on silica and purified by silica gel column chromatography, the mobile phase being a ethyl acetate/hexane mixture in a ratio of 3:7, resulting in the pure title compound (1.89 g, yield 67 %) which was characterised by its mass spectrum as follows: MS (m/z): 172, 174 ([M+H]+, 100).Method B: To a suspension of 6-chloro-3-nitro-pyridine-2-carbonitrile (9.2 g, 50 mmol) in water (100 ml), was added 20 ml of a 25 % ammonia aqueous solution. The mixture was stirred at room temperature for 20 minutes. Then, Na2S2O4 (50 g, 86 %, 150 mmol) was added portion wise, and the mixture was stirred at room temperature for another 2 hours. The precipitate formed was collected by filtration, washed two times with cold water (10 ml) and then dried over P2O5, resulting in the title compound (7.0 g, yield 81 %) as a yellowish solid which was characterized by its mass spectrum as follows: MS (m/z): 172.1 ([M+H]+, 100).; Example 222 – synthesis of S-amino-e-chloro-pyridine^-carboxamideEither of the two following methods may be used:Method A: to a suspension of theta-chloro-S-nitro-pyridine^-carbonitrile (4 g, 22 mmol) in water (40 ml) was added a 33 % aqueous solution of ammonia in water (8.8 ml). This suspension was stirred at room temperature for 30 minutes. Then, sodium dithionite (21.8 g, 124 mmol) was added portion wise. The resulting mixture was stirred for another 2 hours at room temperature. The precipitate was filtered off and washed with a small amount of water, yielding the title compound (2.7 g, yield: 72 %). MS (m/z): 172, 174 ([M+H]+, 100).Method B: to a suspension of e-chloro-S-nitro-pyridine^-carbonitrile (11.01 g, 60 mmol) in methanol (120 ml), was added Raney-Nickel (3 g, washed with methanol EPO to remove water) and the mixture was shaken under a H2-atmosphere at room temperature for 4 hours. The catalyst was removed by filtration, washed with methanol (500 ml). Both filtrates were combined and then evaporated to dryness. The residue was dissolved in dichloromethane and the solution was filtered through a short and wide column with silica gel (100 g). The column was additionally washed with CH2CI2/Me0H (200 ml, 4:1). The filtrate and washings were combined and evaporated to small volume. The formed precipitate was filtered off to give 3-amino-6- chloro-pyridine-2-carboxamide (8.1 g). The final filtrate was evaporated to dryness and the residue purified by column chromatography on silica gel (30 g). The compound was eluted with the following solvent systems: CH2CI2 (200 ml), CH2CI2/Me0H 100:1 (200 ml). The appropriate fractions were evaporated in vacuo yielding an additional 1.15 g of S-amino-theta-chloro-pyridine^-carboxamide (total yield : 9.25 g, i.e. 90 %) which was characterised as follows:- M.p. 176-177C; – UV (MeOH): 212 (3.76), 256 (4.14), and 348 (3.76); and- elemental analysis: calculated for C6H6CIN3O (171.6): C 42.00 H 3.52 N 24.49. Found: C 42.42 H 3.54 H 24.11.

With the rapid development of chemical substances, we look forward to future research findings about 93683-65-9.

Reference:
Patent; 4 AZA Bioscience nv; WO2006/135993; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 462-08-8, Pyridin-3-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, Recommanded Product: Pyridin-3-amine, blongs to pyridine-derivatives compound. Recommanded Product: Pyridin-3-amine

To a solution of pyridin-3 -amine (2.5 g, 26.3 mmol) in anhydrous tetrahydiOfuran (80 mL) was added 1 M sodium bis(trimethylsilyl)amide in tetrahydrofuran (52.6 mL, 52.6 mmol) in a steady stream. The mixture was stirred for 30 minutes, treated dropwise with a solution of di-feri-butyl dicarbonate (5.92 g, 26.3 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 3 hours and concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride, dried over anhydrous MgSCu, filtered, and concentrated by rotary evaporation. Purification by chromatography on silica eluting with 3%> methanol in dichloromethane afforded an amber semisolid. The material was dissolved in ethyl acetate, treated with decolorizing charcoal and vacuum filtered through diatomaceous earth. Concentration of the filtrate by rotary evaporation afforded the title compound as a light gold solid (4.35 g, 85%). MS (DCI+) m/z 195 (M+H)+.

The synthetic route of 462-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH & CO.KG; MARING, Clarence J.; PRATT, John K.; CARROLL, William A.; LIU, Dachun; BETEBENNER, David A.; HUTCHINSON, Douglas K.; TUFANO, Michael D.; ROCKWAY, Todd W.; SCHOEN, Uwe; PAHL, Axel; WITTE, Adreas; WO2012/87833; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-71-0 ,Some common heterocyclic compound, 1122-71-0, molecular formula is C7H9NO, 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 mixture of N3-methyl-N5-(( 15, 25)-2-methylcyclopropyl)-2-oxo- 1,2-dihydropyridine-3,5-dicarboxamide (42.8 mg, 0.17 mmol), (6-methylpyridin-2-yl)methanol (26.9 mg, 0.22 mmolcommercially available from, for example, Sigma-Aldrich) and 2- (tributylphosphoranylidene)acetonitrile (0.090 mL, 0.34 mmol; commercially available from, for example, TCI) in toluene (1 mL) in a sealed vial was heated at 100 C for 0.5 h in a microwave reactor. The volatiles were evaporated from the mixture under a stream of nitrogen and the residuewas redissolved in 3:1 methanol/DMSO (2 mL) and was purified by MDAP (2 x 1 mL injection, formic). The required fractions from both injections were combined, evaporated and dried in vacuo to give a dark brown oily residue. The residue was redissolved in 3:1 methanol/DMSO (1 mL) and was further purified by MDAP (1 x 1 mL injection, formic). The required fractions were combined, evaporated and dried in vacuo to give a pale yellow glass; N3-methyl-N5-((15,25)-2-methylcyclopropyl)-1-((6-methylpyridin-2-yl)methyl)-2-oxo- 1, 2-d ihydropyrid ine-3,5-d icarboxamide (42.2 mg, 0.12 mmol, 69 % yield).LCMS (2 mm formic) Rt = 0.63 mi m/z= 355 for [MH]

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. 1122-71-0, 6-Methyl-2-pyridinemethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); 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. 75418-74-5, name is Methyl 3-oxo-3-(pyridin-2-yl)propanoate. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

a Pyridin-2-yl-propynoic acid ethyl ester The title compound was synthesised from commercially available 3-oxo-3-pyridin-2-yl-propionic acid methyl ester using the procedure described in Example 32, step (b), in 76% yield. 1H NMR (CDCl3) delta8.66 (d, J=4.8 Hz, 1H), 7.73 (m, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.36 (m, 1H), 4.31 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.1 Hz, 3H).

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, 75418-74-5, Methyl 3-oxo-3-(pyridin-2-yl)propanoate.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2002/169200; (2002); 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. 38940-62-4, name is 3-Acetyl-5-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Acetyl-5-bromopyridine

A solution of 1-(5-bromopyridin-3-yl)ethanone (2.04 g, 27.5 mmol) in methanol (55 mL) was added slowly to a cold solution of 2-oxoacetic acid (2.04 g, 27.5 mmol) and potassium carbonate (7.22 g, 52.24 mmol) in water (50 mL). The mixture was stirred at room temperature for 2h. The resultant solution was partially evaporated under reduced pressure at 30 C to remove most of the methanol and then extracted three times with ethyl acetate. The cooled aqueous solution was carefully treated with acetic acid (11 mL, 192 mmol) and washed with dichloromethane. Ethylhydrazine oxalate (3.61 g, 26.1 mmol) was added to the aqueous phase, and the mixture heated under reflux for 2 h. A further 3.61 g ethylhydrazine oxalate (26.12mmols) was added and the mixture heated under reflux for 2 d. The solution was neutralised with potassium carbonate to pH 7 and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure and the crude purified in a 40M column from Biotage on a SP1 automatic purification system using hexane and ethyl acetate as solvents (0-100% ethyl acetate) in 20 column volumes. The appropriate fractions were collected and evaporated to give 3.71 g (47% yield) of the title compound. HPLC/MS (9 min) retention time 5.32 min. LRMS: m/z 282 (M+1)

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, 38940-62-4, 3-Acetyl-5-bromopyridine.

Reference:
Patent; Almirall, S.A.; EP2196465; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 945557-04-0, 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.945557-04-0, name is 5-Bromo-3-chloropicolinonitrile, molecular formula is C6H2BrClN2, molecular weight is 217.4505, as common compound, the synthetic route is as follows.

Acetyl 2,4,6-tri-O-acetyl-3 -azido-3 -deoxy- 1 -thio-cL-D-galactopyranoside (250 mg, 0.64 mmol) and 5-bromo-3-chloro-pyridine-2-carbonitrile (280 mg, 1.28 mmol) were dissolved in DMF (10 mL). Diethylamine (0.15 ml) was added. The reaction was stirred at room temperature with for 20 h. Water (50 mL) and DCM (50 mL) were added. The aqueous phase was extracted with DCM (50 mL X 2), the combined organic phases were washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=3/1) to obtain the product (130 mg, 38%).5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18CLN5O7S] [M+H]: 484.0; found: 484.0.5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-cL-D- galactopyranosidein/z calcd for [C18H18BrN5O7S] [M+H]: 528.0; found: 528.0. To a mixture of 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1- thio-cL-D-galactopyranoside and 5 -Bromo-2-cyano-3 -pyridyl 2,4,6-tri-O-acetyl-3 – azido-3-deoxy-1-thio-cL-D-galactopyranoside (130 mg) in CH3CN (5 mL) were added DIEA (0.23 mL), Copper(I)Iodide(15 mg, 0.08 mmol), CsF(82 mg, 0.54 mmol), 2-(4- chloro-3 ,5 -difluoro-phenyl)ethynyl-trimethyl-silane( 132 mg, 0.54 mmo 1). The reaction was stirred at room temperature for 20 h under a N2 atmosphere. Water (10 mL) and DCM (10 mL) were added. The aqueous phase was extracted with DCM (5 mL X 2), the combined organic phases were washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a residue. The residue was purified by column chromatography (PE/EA=2/1) to obtain the products 110 (80mg) and 111 (20mg).110) 5-Chloro-6-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-a-D-galactopyranosidem/z calcd for [C26H21Cl2F2N5O7S] [M+H]: 656.0; found: 656.0.1H NMR (400 MHz, CDC13) oe 8.63 (d, J 1.9 Hz, 1H), 8.01 (d, J 2.0 Hz, 1H), 7.83 (s, 1H), 7.45 (t, J= 6.3 Hz, 2H), 6.34 (d, J 5.5 Hz, 1H), 6.16 (dd, J 11.7, 5.6 Hz, 1H), 5.63 (d,J= 2.3 Hz, 1H), 5.20 (dd,J= 11.7, 3.1 Hz, 1H), 4.78 -4.71 (m, 1H), 4.14 (tdd, J= 12.8, 8.7, 4.4 Hz, 3H), 2.08 (s, 3H), 2.00 (s, 3H), 1.98 (s, 3H).ill) 5-Bromo-2-cyano-3-pyridyl 2,4,6-tri-O-acetyl-3-deoxy-3- [4-(4-chloro-3,5- difluorophenyl)- 1H- 1 ,2,3-triazol- l-ylj – 1-thio-cL-D-galactopyranosidem/z calcd for [C26H2iBrCIF2N5O7S] [M+H]: 700.0; found: 700.0.

Statistics shows that 945557-04-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-chloropicolinonitrile.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; NILSSON, Ulf; LEFFLER, Hakon; (105 pag.)WO2018/11094; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 779345-37-8, Adding some certain compound to certain chemical reactions, such as: 779345-37-8, name is 5-Fluoro-2-nitropyridine,molecular formula is C5H3FN2O2, 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 779345-37-8.

Synthesis of compound 224.1. To a solution of 220.1 (0.300g, 2.1 lmmol, l .Oeq) in DMSO(5ml) was added 2-methylpropan-2-amine (0.185g, 2.533mmol, 1.2eq.) and DIPEA (2.72g, 21.1 lmmol, lO.Oeq.). The reaction mixture was heated at 100 C for lh. After completion of reaction, mixture was poured in water, quenched with NH4C1 solution and extracted with EtOAc. Organic layers were combined, dried over sodium sulphate and concentrated under reduced pressure to obtain crude which was purified by chromatography to get pure 224.1 (0.225g, 54.59%). MS(ES): m/z 195.22 [M+H]+.

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. 779345-37-8, 5-Fluoro-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2875-18-5, Adding some certain compound to certain chemical reactions, such as: 2875-18-5, name is 2,3,5,6-Tetrafluoropyridine,molecular formula is C5HF4N, 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 2875-18-5.

General procedure: To a solution of fluoroarene (0.1 M) and HSiEt3 (0.1 M) in benzene-d6 in a PFA tube alpha,alpha,alpha-trifluorotoluene (1?2 muL) was added as internal standard. The PFA tube was closed by a Teflon plug, inserted into an NMR tube and an initial 19F{1H} NMR spectrum was recorded. Then [Rh(mu-H)(dippp)]2 (1) (0.005 M) was added and the reaction mixture was heated to 50 °C for 48 h. Hydrodefluorination of pentafluoropyridine gave 2,3,5,6-tetrafluoropyridine (11percent), 2,3,4,5-tetrafluoropyridine (11percent), 2,3,5-trifluoropyridine (8percent), 3,5-difluoropyridine (6percent) and 2-fluoropyridine (1percent) (TON = 11). Hydrodefluorination of 2,3,5,6-tetrafluoropyridine or 2,3,5,6-tetrafluoropyridine or 2,3,5,6-tetrafluoropyri-dine gave 2,3,5-trifluoropyridine (24percent), 2,3,6-trifluoropyridine (7percent), 3,5-difluoropyridine (15percent), 2,5-difluoropyridine (2percent) and 2-fluoropyridine (8percent) (TON = 18). Hydrodefluorination of hexafluoro-benzene or hexafluoroben-zene or hexa-fluorobenzene gave pentafluorobenzene (12percent) and 1,2,4,5-tetra-fluorobenzene or 1,2,4,5-tetrafluoro-benzene or 1,2,4,5-tetrafluoroben-zene (2percent) (TON = 3.1). Hydrodefluorination of pentafluorobenzene gave 1,2,4,5-tetrafluorobenzene (35percent), 1,2,3,4-tetrafluorobenzene (3percent), 1,2,4-trifluorobenzene (23percent) and 1,4-difluorobenzene (4percent) (TON = 19). Yields of organic hydrodefluorination products were determined from 19F{1H} NMR spectra by integration of product resonances versus the internal standard. Hydrodefluorination products were identified by NMR spectroscopy by comparison with literature data [23]. TON: number of hydrodefluorination steps/moles of 1.

According to the analysis of related databases, 2875-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Za?mostna?, Lada; Ahrens, Mike; Braun, Thomas; Journal of Fluorine Chemistry; vol. 155; (2013); p. 132 – 142;,
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.875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.name: 5-Bromo-1H-pyrazolo[3,4-b]pyridine

Step 4: Synthesis of 5-bromo-3-iodo-lH-pyrazolo[3,4-b]pyridine.[0220] 5-bromo-17J-pyrazolo[3,4-b]pyridine (3.00 g, 15.2 mmol) and A’-iodosuccinimide(3.60 g, 16.0 mmol) were dissolved in anhydrous dichloroethane (100 mL). The resultingmixture was stirred under reflux conditions for 6 h, cooled to room temperature and dilutedwith THF (300 mL). The resulting solution was washed with a saturated aqueous solutionof sodium thiosulfate (100 mL) and brine, then dried over magnesium sulfate, filtered andconcentrated. The residue was titurated with a 1:1 mixture of dichloromethane and etherand then ether before being dried in vacuum to afford 5-bromo-3-iodo-l//-pyrazolo[3,4-bjpyridine (3.795 g, 77% yield) as a beige-brown solid. ^-NMR (500 MHz, Patent; SGX PHARMACEUTICALS, INC.; WO2006/15124; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem