Day: June 3, 2021

Synthetic Route of 63725-51-9, 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 63725-51-9, name is 6-Chloro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate Gen-19-a (5 g, 32.6 mmol, 1 eq) is dissolved in DMF (30 mL). I2 (16.4 g, 64.6 mol, 2 eq) and KOH (6.8 g, 121 mmol, 3.7 eq) are added. The reaction mixture is stirred at rt for 3 h. Then the reaction is quenched with a 10% solution of Na2S2O3. The aqueous layer is extracted four times with 50 mL Et2O, three times with DCM and three times with DCM/ MeOH 9:1. The combined organic layers are dried over Na2SO4, after washing with brine (50 mL), filtered and concentrated to afford Gen-20-a.

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 63725-51-9, 6-Chloro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; SANIERE, Laurent Raymond Maurice; HUCK, Jacques; DYKES, Graeme James; SCHMITT, Benoit Antoine; BLANC, Javier; BUTLER, Anna Sara; BONNATERRE, Florence Marie-Emilie; BEAUMONT, Stephane Nicolas Alain; US2015/80391; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128071-98-7 ,Some common heterocyclic compound, 128071-98-7, molecular formula is C5H3BrFN, 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.

[00208] Step 1 : To a solution of 4-bromo-2-fluoropyridine (5.0 g, 28.4 mmol) in DMSO (56.8 mL, 28.4 mmol) was sequentially added tetrahydro-2H-pyran-4-amine (3.30 g, 32.7 mmol) and cesium carbonate (18.5 g, 56.8 mmol). The mixture was then stirred at 80 C for 4 hours and cooled to ambient temperature. The mixture was then poured into water and extracted into EtOAc (200 mL). The combined organics were washed with half saturated brine (50 mL), dried (MgS04), filtered and concentrated in vacuo. The crude isolated was purified by flash chromatography (Ready Sep 120 g) eluting with a gradient of 1-10% MeOH:DCM (10 CV) to provide 4-bromo-N-(tetrahydro-2H-pyran-4-yl)pyridin-2 -amine (2.80 g, 38.3% yield). LCMS (APCI+) m/z 257, 259 (M+l) with one bromine isotope.

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. 128071-98-7, 4-Bromo-2-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; COOK, Adam; GAUDINO, John; GUNAWARDANA, Indrani, W.; HICKEN, Erik, James; HUNT, Kevin, W.; LYON, Michael; METCALF, Andrew, T.; MOHR, Peter, J.; MORENO, David, A.; NEWHOUSE, Brad; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; GAZZARD, Lewis; SCHMIDT, Jane; DO, Steve; WO2015/103137; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1222185-12-7, 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 1222185-12-7 as follows.

(E)-Dimethyl 3-styrylpyridine-2,4-dicarboxylate Z4’A stirred suspension of 3-bromopyridine 11 (500 mg, 1.82 mmol, 1 eq.), (E)-styryl boronic acid (300 mg, 2.01 mmol, 1.1 eq.), Cs2CO3 (650 mg, 2.01 mmol, 1.1 eq.), Pd(OAc)2 (40 mg,0.182 mmol, 0.1 eq.) and PPh3 (100 mg, 0.365 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 0C for 5 h in an oil bath. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo.The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EpsilontOAc/hexane) to afford Z4′ (322 mg, 60%) as an off-white solid.1U NMR deltaH (400 MHz; CDCl3) 3.86 (s, 3H, OCH3), 3.89 (s, 3Eta, OCH3), 6.59 (d, J=16.5 Hz, IH, CH=CH), 7.23-7.30 (t, J=8.0 Hz, IH, ArHpara), 7.34 (t, J=8.0 Hz, 2H, ArHmeta), 7.46 (d, J=7.0 Hz, 2H, ArHortho), 7.64 (d, J=16.5 Hz, IH, CH=CH), 7.71 (d, J=5.0 Hz, IH, pyHmeta), 8.65 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.8 (CH3), 52.8 (CH3), 123.5 (CH=CH), 124.6 (ArCH), 126.7 (ArCH), 128.4 (ArCH), 128.7 (ArCH), 133.0 (ArQ, 135.1 (CH=CH), 136.5 (ArQ, 139.0 (ArQ, 147.9 (ArCH), 149.8 (ArQ, 166.5 (CO), 166.7 (CO); IR vmax (filmycrn 1 2953, 1735, 1447, 1434, 1313, 1269, 1197, 1166, 1143, 1130; HRMS (EpsilonSI+) for C17H15NNaO4 requires 320.0893, found (M+Na*) 320.0893;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1222185-12-7, its application will become more common.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, 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 6 Synthesis of 2-fluoro-5-[(E)-2-(4-methoxyphenyl)vinyl]pyridine (1f); Compound 1f was synthesized by Horner-Wadsworth-Emmons.10Synthe -fluoro-5-[(E)-2-(4-methoxyphenyl)vinyl1pyridine (1f)To a solution of diethyl [4-(meththoxy)benzyl]phosphonate (500 mg, 1 .94 mmol) and 6-fluoropyridine-3-carbaldehyde (242 mg, 1 .94 mmol) in DMF (4 mL) was added a solution of potassium tert.butylat (543 mg, 4.8 mmol) in DMF (16 mL). After stirring for one hour the reaction mixture was quenched with saturated aqueous ammonium chloride solution, extracted with dichloromethane, washed with brine and dried over sodium sulfate. The residue was purified by chromatography on silica gel (ethyl acetate in hexane 0 to 50%) to yield 50.6 mg (10.3%) of the title compound.1 H-NMR (400 MHz, CHLOROFORM-d) d = 3.85 (s, 3H), 6.92 (d, 1 H), 6.92 (dd, 1 H), 6.93 (d, 2H), 7.05 (d, 1 H), 7.46 (d, 2H), 7.93 (ddd, 1 H), 8.28 (d, 1 H) ppm. 19F-NMR (376 MHz, CHLOROFORM-d) delta = -70.13 (d, 1 F) ppm. MS ES+ m/z = 230.13 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BERNDT, Mathias; BROCKSCHNIEDER, Damian; HEINRICH, Tobias; BERGER, Markus; WO2011/141515; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 614-18-6, Adding some certain compound to certain chemical reactions, such as: 614-18-6, name is Ethyl nicotinate,molecular formula is C8H9NO2, 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 614-18-6.

EXAMPLE 58 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70 C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours The resulting white solid was removed by filtration, affording 46 g 15 (85 1%) of the title compound melting at 75-78 C.

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. 614-18-6, Ethyl nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Florida; US5017566; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14529-54-5, Adding some certain compound to certain chemical reactions, such as: 14529-54-5, name is 3,5-Dibromo-1-methylpyridin-2(1H)-one,molecular formula is C6H5Br2NO, 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 14529-54-5.

Example 304c 5-Bromo-3-(5-(2-methoxyethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-1-methylpyridin-2(1H)-one 304c A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 304b (230 mg, 1.17 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (468.4 mg, 1.76 mmol), Pd2(dba)3 (53.5 mg, 0.0585 mmol), Xantphos (67.6 mg, 0.117 mmol), Cs2CO3 (762.8 mg, 2.34 mmol), and dioxane (20 mL). After three cycles of vacuum/N2 flush, the mixture was heated at 100C for 3 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. It was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 304c as a dark solid (380 mg, 85%). MS-ESI: [M+H]+ 382.2

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. 14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
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. 16063-69-7, name is 2,4,6-Trichloropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,4,6-Trichloropyridine

To a solution of 2,4,6-trichloropyridine (3.64 g, 20.0 mmol) in DMF (20 mL) at 0C were slowly added NaH (60% in mineral oil, 840 mg, 21 mmol) and MeOH (673 mg, 21 mmol). The mixture was stirred at room temperature for 16 h. The mixture was concentrated and partitioned between EtOAc (30 mL) and water (15 mL). The organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with ethyl acetate in hexane (0-5 percent) to afford the title compound (3.0 g, yield: 94%).

The synthetic route of 16063-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEW ERA PHARMA, INC.; XIAN, Jun; (82 pag.)WO2018/106459; (2018); 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.135795-46-9, name is 3-Amino-2-bromo-6-methoxypyridine, molecular formula is C6H7BrN2O, molecular weight is 203.04, as common compound, the synthetic route is as follows.Safety of 3-Amino-2-bromo-6-methoxypyridine

2-Bromo-6-methoxypyridin-3-amine (315.6g, 1.56mol, 1.00wt) was charged to a 20000mL flask under nitrogen followed by tetrahydrofuran (2000mL, 6.3vol) and the reaction mixture cooled to -5oC. Sodium bis(trimetylsilylamide) (1M solution in tetrahydrofuran, 3400mL, 3.42mol, 10.9vol) was added dropwise over 2 hours maintaining the temperature below 5oC. The reaction was warmed to room temperature and stirred for 1 hour. The mixture was re-cooled to 0-5oC and di-tert butyl dicarbonate (372.4g, 1.72mol, 1.18wt) solution in tetrahydrofuran (1600mL) added dropwise over 1 hour. The reaction was left to stir under nitrogen over 16 hours after which the 1H-NMR showed complete reaction. Ethanol (6000mL, 19vol) was added to quench the reaction mixture, stirred for 1 hour and concentrated. Dichloromethane (18000mL, 57vol) and saturated ammonium chloride (3000mL, 9.5vol) were charged to the reaction vessel and stirred for 15 minutes. The layers separated and the aqueous layer extracted with dichloromethane (3x 2000mL, 6.3vol). The combined organic fractions were washed with saturated brine (4000mL, 12.7vol), dried over magnesium sulphate, (315g, 1wt), filtered and concentrated under to give a dark red solid (551.4g).The crude product was purified by dry flash chromatography on silica (2x 2200kg, 8wt) eluting with ethyl acetate:heptanes (1:19; Rf 0.28) collecting 2000mL fractions (TLC visualised at UV 254nm and developed by KMNO4). The product containing fractions were combined and concentrated under reduced pressure to give the title compound 19 (368.6g, 78.2%) as a red solid.1H NMR (400MHz, DMSO): d 1.57 (s, 9H), 3.94 (s, 3H), 6.97 (d, J=8.1Hz, 1H), 7.71 (d, J=8.1Hz, 1H), 8.71 (br s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135795-46-9, 3-Amino-2-bromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Article; Badland, Matthew; Devillers, Ingrid; Durand, Corinne; Fasquelle, Veronique; Gaudillire, Bernard; Jacobelli, Henry; Manage, Ajith C.; Pevet, Isabelle; Puaud, Jocelyne; Shorter, Anthony J.; Wrigglesworth, Roger; Tetrahedron Letters; vol. 52; 41; (2011); p. 5292 – 5296;,
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. 188554-13-4, name is 2-Hydroxyisonicotinaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-Hydroxyisonicotinaldehyde

4-[(E)-2-(4-Fluoro-phenyl)-vinyl]-pyridin-2-ol:To a solution of dieihyl-4-fI?iorobenzyl-phosphonatc (515 mg, 2.09 mmol) in THF ( 10.0 mL) was added potassium tert-buloxide (246 mg, 2.09 mmol). After stirring at 20 0C for 1 h, the mixture was treated with 2-hydroxypyridoaIdehyde (246 mg, 2.00 mmol), and allowed to stir for 3 h at 20 0C. The reaction mixture was quenched with water, and the aqueous phase was extracted with DCM, the combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude oil was purified by column chromatography (DCM to 20%methanol in DCM) gave the desired product 4-[(L)-2-(4-fluoro-phenyO-vinyl]-pyridin-2-ol (32.0 mg, 7.5%, 5: 1 transxis) as white crystal. 1H NMR (400 MHz, CDCh) ?: 7.56 (m, 2H), 7.33 (m, I H), 7.26 (m, IH), 7.08 (m, 2H), 6.87 (m, IH), 6.64 (m, IH), 6.54 (m, IH); ESMS m/e: 216 (M+H)+.

The synthetic route of 188554-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2009/120655; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5223-06-3, 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. 5223-06-3, name is 2-(5-Ethylpyridin-2-yl)ethanol, molecular formula is C9H13NO, 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.

(a) To a solution of 2-(5-ethyl-2-pyridyl)ethanol (53.0 g) and 4-fluoronitrobenzene (47.0 g) in DMF (500 ml) was added portionwise under ice-cooling 60% sodium hydride in oil (16.0 g). The mixture was stirred under ice-cooling for one hour, then at room temperature for 30 minutes, poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4). The solvent was evaporated off to give 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene as crystals (62.0 g, 62.9%). Recrystallization from ether-hexane gave colorless prisms, m.p. 53-54 C.

According to the analysis of related databases, 5223-06-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4687777; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem