Category: pyridine-derivatives

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. 17228-64-7, name is 2-Chloro-6-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 17228-64-7

General procedure: A heating reaction vessel was charged with the prescribed amount of catalyst, naphthylpyrimidine (0.5 mmol), aryl chloride (0.6 mmol), K2CO3 (1.5 mmol), KO2CR (0.1 mmol), PAr3 (0.1 mmol) and water (3 mL) under nitrogen. The vessel was sealed and heated at 120 C (oil bath temperature) for 24 h. The resulting mixture was cooled to room temperature, and the aqueous layer was extracted with ethyl acetate, then the combined organic layers were washed with water, dried over MgSO4, filtered, and the solvent was removed on a rotary evaporator. The resulting residue was purified by flash chromatography to give the corresponding products 1-34.

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, 17228-64-7, 2-Chloro-6-methoxypyridine.

Reference:
Article; Li, Hong-Mei; Tu, Tian-Yong; Han, Xin; Wang, Zhi-Qiang; Fu, Wei-Jun; Hao, Xin-Qi; Song, Mao-Ping; Xu, Chen; Synlett; vol. 29; 13; (2018); p. 1729 – 1734;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 183208-35-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 183208-35-7 as follows.

Into a 500 mL round bottomed flask were added 5-bromo-1H-pyrrolo[2,3-b]rhoyridine (10.11 g, 51.3 mmol) and 250 ml acetone. N-iodosuccinimide (NIS, 12.7 g, 56.4 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The precipitate was collected and washed with cold acetone to afford 12. 2 g (74%) of the title compound as a tan powder. 1H-NMR (500 MHz, ^6-DMSO) J= 12.35 (br.s, 1H), 8.29 (d, J=2.0 Hz, 1H), 7.84 (d, J=2.0 Hz 1 H), 7.79 (s, 1H); MS: m/z 322.8/324.8 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2008/124849; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886364-86-9, 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. 886364-86-9, name is 5-Bromo-4-methylpicolinonitrile, molecular formula is C7H5BrN2, 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.

5-bromo-4-methyl-2-(2H-tetrazol-5-yl)-pyridine:To a mixture of 5-bromo-4-methylpicolinonitrile (2.5 g, 12.7 mmol, Eq: 1.00), sodium azide (1.07 g, 16.5 mmol, Eq: 1.3) and triethylamine hydrochloride (2.27 g, 16.5 mmol, Eq: 1.3) was added xylene (25 ml). The reaction mixture was heated at 140 C. overnight, and upon cooling was concentrated under reduced pressure. To the white residue was added water and an aq. HCl solution. These solids were filtered, washed with water, and dried to give 5-bromo-4-methyl-2-(2H-tetrazol-5-yl)-pyridine (2.43 g, 80% yield) as an off-white solid.

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 886364-86-9, 5-Bromo-4-methylpicolinonitrile.

Reference:
Patent; Hoffmann-La Roche Inc; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90334; (2013); 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.104408-24-4, name is 6-Hydrazinylnicotinonitrile, molecular formula is C6H6N4, molecular weight is 134.1386, as common compound, the synthetic route is as follows.Safety of 6-Hydrazinylnicotinonitrile

[1086] a mixture of ethyl 2-(methoxyimino)-4-oxopentanoate (558.2 mg, 2.98 mmol) and 6-hydrazinylnicotinonitrile (400 mg, 2.98 mmol) in AcOH (5 ml) was stirred at 118 C for 5 hours. The reaction mixture was cooled to 25 C and concentrated under reduced pressure to give a residue, which was diluted with ch2ci2 (100 ml). The organic phase was washed with saturated aqueous NaHCO3 (20 ml), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue, which was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 1 :0 to 5: 1) to afford compound 208a (160 mg, 19.09% yield) as a white solid, but structure (proposed structure) could not be confirmed by n-h hmbc. 1H NMR (400 mhz, CDCl3): delta 8.66 (dd, = 0.8, 2.4 hz, 1h), 8.07 (dd, j = 2.4, 8.4 hz, 1h), 7.88 (dd, j = 0.8, 8.4 hz, 1h), 6.67 (s, 1h), 4.35 (q, j = 6.8 hz, 2h), 2.37 (s, 3h), 1.32 (t, j = 7.2 hz, 3h). MS (ESI) m/z (m+l)+ 257.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,104408-24-4, 6-Hydrazinylnicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 93683-65-9, 6-Chloro-3-nitropicolinonitrile, 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, Product Details of 93683-65-9, blongs to pyridine-derivatives compound. Product Details of 93683-65-9

Example 6b 3-nitro-6-thioxo-1,6-dihydropyridine-2-carbonitrile One equivalent of NaSH:H2O is added to a solution of 6-chloro-3-nitropicolinonitrile (5.45 mmol, 1 g) in 20 ml of EtOH. The color turns orange. The reaction medium is stirred at room temperature for 30 minutes. The crude reaction product is then concentrated, redissolved in ethyl acetate and extracted several times using an acidic aqueous phase (1 N HCl) and then a neutral phase. The organic phase is concentrated and the crude reaction product recrystallized in acetone to yield 0.64 g (79%) of yellow crystals. 1H NMR: deltaH ppm (400 MHz, DMSO): 8.71 (1H, d, CHarom), 8.27 (1H, d, CHarom).

The synthetic route of 93683-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; US2013/85144; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6271-78-9, 6-Chloropyridine-3-carboxamide, 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, Quality Control of 6-Chloropyridine-3-carboxamide, blongs to pyridine-derivatives compound. Quality Control of 6-Chloropyridine-3-carboxamide

A solution of 6-chloronicotinamide (15 g, 95.8 mmol) and hexamethyleneimine(11.4 g, 115 mmol) in DMSO (20 mL) was heated at 60 oC for 12 hours afterwhich TLC indicate complete consumption of the starting material. The mixturewas diluted with water which resulted in the formation of a thick precipitate andrequired further dilution to give a free-flowing mixture to filter (300 mL water).The solid was filtered off and washed with water (50 mL). The solid wasdissolved in DCM (500 mL) and EtOAc (500 mL), dried (Na2SO4), filtered, andconcentrated in vacuo. The resulting solid was suspended in EtOAc and filteredto give 13 as a beige crystalline solid (12 g, 57%).1H NMR (400 MHz, DMSO-d6): delta 1.4 – 1.5 (m, 4H), 1.6 – 1.7 (m, 4H), 3.5 – 3.7(m, 4H), 6.6 (d, J = 9.2 Hz, 1H), 7.0 (br s, 1H), 7.6 (br s, 1H), 7.9 (dd, J = 2.4 Hz,J = 9.2 Hz, 1H), 8.5 (d, J = 2.4 Hz, 1H). 13C NMR (100 MHz, DMSO-d6): delta 26.8,27.4, 47.6, 104.5, 117.2, 137.0, 149.0, 159.3, 167.5. MS (ESI) m/z: [M – H]+Calculated for C12H16N3O: 218.27; Found: 218.4. Purity: >99.0%.

The synthetic route of 6271-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jalily, Pouria H.; Eldstrom, Jodene; Miller, Scott C.; Kwan, Daniel C.; Tai, Sheldon S.-H.; Chou, Doug; Niikura, Masahiro; Tietjen, Ian; Fedida, David; Molecular Pharmacology; vol. 90; 2; (2016); p. 80 – 95;,
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.1970-81-6, name is [3,3′-Bipyridine]-5-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.Recommanded Product: 1970-81-6

Referring to Scheme 1, synthesis of compound 13, to a cooled (0C) suspension of compound 2 (0.6 g, 3.0 mmol) in dichloromethane (100 mL), was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.69 g, 3.6 mmol), 1-hydroxy-benzotriazole hydrate (0.49 g, 3.6 mmol), and triethylamine (0.5 mL, 3.6 mmol). After stirring for 30 min. at 0C (the reaction became almost clear), compound 9 (0.4 g, 1.2 mmol) and triethylamine (1.0 mL, 7.2 mmol) were added. The reaction was stirred for 16 h., then washed with saturated NaHCO3 (3 x 50 mL). The DCM layer was dried with MgSO4, reduced in volume in vacuo, and purified by flash column chromatography (2% – 25% methanol in DCM) to give compound 13 (90 mg, 12%). 1H NMR (CDCl3, 500 MHz) delta 1.70 (m, 2H), 1.75 (m, 2H), 1.87 (m, 2H), 1.89 (s, 3H), 1.98 (m, 1H), 2.14 (m, 1H), 3.28 (m, 1H), 3.35 (m, 1H), 3.40 (m, 2H), 3.64 (m, 1H), 3.70 (m, 1H), 4.85 (q, J = 4.9 Hz, 1H), 5.30 (s, 1H), 5.67 (s, 1H), 6.40 (t, J = 5.0 Hz, 1H), 7.36 (t, J = 5.0 Hz, 1H), 7.42 (dd, J = 3.9, 2.2 Hz, 1H), 7.43 (dd, J = 3.9, 2.2 Hz, 1H), 7.65 (t, J = 4.45 Hz, 1H), 7.72 (d, J = 6.1 Hz, 1H), 7.93 (d, J = 1.5 Hz, 1H), 7.95 (d, J = 1.5 Hz, 1H), 8.42 (m, 2H), 8.67 (dd, J = 4.1, 1.0 Hz, 1H), 8.68 (dd, J = 4.0, 1.2 Hz, 1H), 8.889 (s, 1H), 8.891 (s, 1H), 8.93 (d, J = 1.7 Hz, 1H), 8.96 (d, J = 1.8 Hz, 1H), 9.10 (d, J = 1.6 Hz, 1H), 9.13 (d, J = 1.7 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1970-81-6, [3,3′-Bipyridine]-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MEDTRONIC MINIMED, INC.; GAMSEY, Soya; WESSLING, Ritchie, A.; EP2222686; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16063-69-7, Adding some certain compound to certain chemical reactions, such as: 16063-69-7, name is 2,4,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 16063-69-7.

To a mixture of 2,4,6-trichloropyridine (5 g, 27.5 mmol. 1 eq), morpholine (7.2 mL, 82.3mmol, 3 eq), sodium tert-butoxide (7.9 g, 82.3 mmol, 3 eq), (2-biphenyl)di-tert-butyl-phosphine (408 mg, 2.7 mmol, 0.05 eq) in tetrahydrofuran (80 mL) was added Pd(dppf)C12 (from Combi-blocks, product number: OT-0746), 1 g, 2.7 mmol, 0.05 eq). The mixture was stirred at 8000 for 4 h. The mixture was cooled down to room temperature and poured onto a saturated solution of NH4CI (100 mL). The phases were separated and theaqueous phase was extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure using a rotary evaporator. Products Bi and B2 were isolated by flash chromatography on silica gel using first a 1:4.5 mixture of ethyl acetate and cyclohexane and then 1:1 mixture of ethyl acetate and cyclohexane as eluent. The product fractionswere pooled and evaporated to yield Bi as an off white powder (2.45 g, 8.6 mmol, 31%)and B2 as an off white powder (2.2 g, 7.8 mmol, 28% yield).

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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITAET BASEL; PIQUR THERAPEUTICS AG; HEBEISEN, Paul; BEAUFILS, Florent; LANGLOIS, Jean-Baptiste; WO2015/162084; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144100-07-2, 2-Bromo-6-fluoropyridine, 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, Quality Control of 2-Bromo-6-fluoropyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-6-fluoropyridine

A solution of 2-bromo-6-fluoropyridine (2.4 g, 13.64 mmol), o-tolylboronic acid (2.039 g, 15.00 mmol) and Tetrakis (0.158 g, 0.136 mmol) in Dioxane was degassed by nitrogen bubble for 10 min. A solution of Phosphoric acid, potassium salt (8.68 g, 40.9 mmol) in H20 (2ml) was then added and the solution heated to reflux for 18 h. The crude material was purified via silica gel chromatography (90g SiOi column, hexane:EtOAc 100:0 -> 90: 10) to afford 2-fluoro-6-(o-tolyl)pyridine, 2.41 g (94percent). NuMuRhonu (400 MHz, CDCb) delta 7.87 (q, J=8.2 Hz, 1H), 7.46 – 7.41 (m, 1H), 7.37 – 7.26 (m, 4H), 6.92 (dd, J=8.2, 2.9 Hz, 1H), 2.43 (s, 3H).

The synthetic route of 144100-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 171178-46-4 , The common heterocyclic compound, 171178-46-4, name is 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid, molecular formula is C11H13ClN2O4, 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.

5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinic acid (Intermediate B) (4.27 g, 15 mmol, 1 equiv.) was added to a 500 mL two necked oven-dried round bottom flask equipped with a stirring bar and suspended in dichloromethane (187 mL, 0.08M) was added. 4-Dimethylamino pyridine (7.40 g, 60 mmol, 4 equiv.) was added at 22C resulting in an homogeneous solution. /V-(3-dimethylaminopropyl)-/V-ethylcarbodiimide (4.65 g, 30 mmol, 2 equiv.) was added at that temperature and the crude mixture was stirred for 3 h. Anhydrous MeOH (HPLC quality), (5.5 mL, 135 mmol, 9 equiv.) was added to the solution and the mixture was stirred for 1 h at 22C. The resulting mixture was heated to reflux using an aluminium heating block for 72 h. TLC (EtOAc:MeOH 90:10 %v/v) showed complete conversion of Intermediate B into Intermediate C. The reaction was permitted to reach to 22C and volatiles were removed under reduced pressure. Dichloromethane (150 mL) was added to the residue until complete solution was achieved and the mixture was transferred to a separating funnel, washed with H2O (1 x 70 mL), HCI 1 M (2 x 50 mL) and saturated NaCI solution (1 x 50 mL). The organic phase was dried with Na2S04 and filtered through a pad of Na2S04 on a filter plate. The solvent was removed under reduced pressure giving a brown solid, which was purified by automated flash chromatography (Heptane:EtOAc, product elution with EtOAc 100%v/v) giving methyl 5-((fe/f-butoxycarbonyl)amino)-2-chloroisonicotinate as a pale yellow solid (4.04 g, 79% yield). Purity: 99.4% (UPLC-A); mp: 90.0-95.8 C; 1H- NMR (CDCI3), 5(ppm): 9.68 (bs, NH), 9.49 (s, 1 H), 7.73(s, 1 H), 7.20 (s, 1 H), 3.91 (s, 3H), 1.47 (s, 9H); LR-MS (ESI+): m/z= 287.1 Da [M+H]+, calcd. for CI2HI5CIN204: 286.2

The synthetic route of 171178-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAES FARMA, S.A.; HERNANDEZ HERRERO, Gonzalo; GARCIA DOMINGUEZ, Neftali; ZAZPE ARCE, Arturo; OLIVERA TIZNE, Roberto; NOVERGES PEDRO, Barbara; CORCOSTEGUI VIVAR, Reyes; TATO CERDEIRAS, Paloma; (124 pag.)WO2020/20939; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem