Tag: M.W:200-300

Application of 946002-90-0, 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.946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, molecular formula is C9H11BrN2O, molecular weight is 243.1, as common compound, the synthetic route is as follows.

(R)-5-Bromo-2-[3-(2,6-dichloro-4-methyl-phenoxy)-pyrrolidin-l-yl]-pyridine. ADDP (11.7 g, 45.4 mmol) was added to a sol. of compound Gl (8.82 g, 36.3 mmol) and 2,6-dichloro-/?-cresol (7.37 g, 40.0 mmol) in toluene (200 mL). The mixture was degassed with nitrogen for 5 min, and PBu3 (85%, 15.8 mL, 46.2 mmol) was added. The mixture was heated rapidly to 100 0C, and stirred at this temperature for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane (200 mL). The mixture was filtered, and the filtrate was evaporated under reduced pressure. Purification of the residue by FC (EtO Ac/heptane 1 :7) yielded a crude title compound that was diluted with CH2Cl2. This mixture was washed with aq. IM NaOH. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the pure title compound (13.5 g, 93%). LC-MS: tR = 0.92 min; ES+: 402.98.

The chemical industry reduces the impact on the environment during synthesis 946002-90-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89282-03-1 ,Some common heterocyclic compound, 89282-03-1, molecular formula is C5H4INO, 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.

Dry DMF (6.0 mL) was added to methyl 4-hydroxy-3-iodobenzoate (0.56 g, 2.0 mmol), ethynylboronic acid MIDA ester (0.47 g, 2.6 mmol), CuI (38 mg, 0.20mmol), PdCl2(Ph3P)2 (70 mg, 0.10 mmol) and Ph3P (52 mg, 0.20 mmol) under N2. 1,1,3,3-Tetramethylguanidine(TMG) (0.30 mL, 2.4 mmol) was added to the resulting solution under N2. The reactionmixture was stirred at 50 Cfor 22 h under N2. The resulting mixture was diluted with water to form aprecipitate, which was filtered, washed with water and dried at room temperature. The obtained solid was dissolved in acetone and purified by flash chromatography (SiO2, CH2Cl2 : MeOH = 10 : 1). The eluted material was washed with hot EtOH and dried to give 1A (493.6 mg, 75%) as a pale brown solid; Furo[3,2-c]-2-boronic acid (13): Prepared from 4-hydroxy-3-iodopyridine and ethynylboronic acidMIDA ester. The resulting mixture was diluted with water and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2,CH2Cl2 : MeOH = 10 : 1) to give 180.7 mg of 1 : 1 mixture of MIDA boronate and boronic acid as a pale yellow powder (41%). The mixture was treated with hot EtOH to afford 13 (109.9 mg, 34%) as a paleyellow solid; IR (cm-1) 3000, 1736, 1616, 1591, 1570, 1541, 1473, 1373, 1356, 1300, 1228, 1164, 1145,1039; 1H-NMR (DMSO-d6) delta 7.57 (d, J = 0.5 Hz, 1H), 7.65 (d, J = 6.0 Hz, 1H), 8.46 (d, J = 6.0 Hz, 1H),9.00 (s, 1H); HRMS calcd for C7H7NO3B [M+H] 164.0514, found 164.0513 (Delta 0.05).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.

Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
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.1163693-01-3, name is 2-Chloro-3-iodo-4-methoxypyridine, molecular formula is C6H5ClINO, molecular weight is 269.47, as common compound, the synthetic route is as follows.Recommanded Product: 2-Chloro-3-iodo-4-methoxypyridine

A solution of 4a3 (33.1 g, 123 mmol), F (7.14 g, 123 mmol) and Cul (23.39 g, 123 mmol) in NMP (165 mL) is heated at 80 C. Methyl-2-chloro-2,2-difluoroacetate (51.8 mL, 491 mmol) is added and the mixture is heated 1.5 h at 120 C. The reaction mixture is poured into brine and Et20 is added. The solid is filtered and the layers separated. The organic layer is washed with water and the aqueous layer is extracted with Et20. The combined organic layers are washed with brine, dried over Na2S04, filtered and concentrated in vacuum followed by Kugelrohr distillation to afford the trifluoromethyl derivative 4a4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1163693-01-3, 2-Chloro-3-iodo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; STAMMERS, Timothy; BARBEAU, Xavier; BEAULIEU, Pierre; BERTRAND-LAPERLE, Megan; BROCHU, Christian; EDWARDS, Paul, J.; FORGIONE, Pasquale; GODBOUT, Cedrickx; HUCKE, Oliver; JOLY, Marc-Andre; LANDRY, Serge; LEPAGE, Olivier; NAUD, Julie; PESANT, Marc; POIRIER, Martin; POIRIER, Maude; THAVONEKHAM, Bounkham; WO2011/32277; (2011); 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. 69045-83-6, name is 2,3-Dichloro-5-(trichloromethyl)pyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2,3-Dichloro-5-(trichloromethyl)pyridine

EXAMPLE 10 2,3-Dichloro-5-(trifluoromethyl)pyridine STR12 A 360 milliliter (ml) TEFLON PFA reaction flask, fitted with a PFA reflux condenser, an HF bleed tube, a magnetic stirrer and an optical pyrometer, was charged with 180 grams (g) of 2,3-dichloro-5-(trichloromethyl)pyridine and 4.3 g (5 mole percent) of FeCl2. Anhydrous HF gas was introduced into the reaction mixture (~4 g/hr) below the surface of the liquid as the reaction mixture was heated to a temperature between 170 C. and 175 C. This temperature (170-175 C.) was maintained for a period of 70 hours with constant agitation. Standard gas-liquid chromatography (GLC) analysis of the product indicated that the reaction product contained:

The synthetic route of 69045-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4590279; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 936011-17-5, 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 936011-17-5 as follows.

[0926] XXV-6 was obtained following the synthetic scheme as described above. MS (ESI) m/z (M+H)+ 231.95.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936011-17-5, its application will become more common.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); 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. 1448427-99-3, name is 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C10H13N5

Alternative Synthesis of Compound (A) Compound (E) (1 equiv.), Compound (C) (1 equiv.), DMF (about 16 vols), Et3N (1.5 equiv.), Pd(OAc)2(0.02 equiv.), and Ad2P(-Bu) (0.04 equiv.) were combined and the contents were purged with N2followed by CO and then pressurized with CO (20 psi). The reaction mixture was heated to about 95 C to about 105 C. After about 24 hours, the reaction was allowed to cool to about 20 C to about 30 C to afford Compound (A).

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, 1448427-99-3, 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine.

Reference:
Patent; GILEAD SCIENCES, INC.; BROWN, Brandon Heath; CHAN, Brenda J. Burke; CHIU, Anna; GRIGGS, Nolan; HEUMANN, Lars V.; LATHROP, Stephen P.; REYNOLDS, Troy Evan; SARMA, Keshab; SILER, David Allen; THOMPSON, Andrew S.; WANG, Tao; (146 pag.)WO2016/106384; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1018505-59-3, 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.1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, molecular weight is 206.2874, as common compound, the synthetic route is as follows.

Preparation of 6-chloro-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine A mixture of impure 5-(4-ethylpiperazin-1-yl)pyridin-2-amine (1.00 g, 4.85 mmol assumed), 8-bromo-6-chloroimidazo[1,2-a]pyridine hydrochloride salt (1.30 g, 4.85 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (634 mg, 1.02 mmol) and cesium carbonate (4.90 g, 15.0 mmol) in toluene (50 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (120 mg, 0.491 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted in a mixture of 1:1 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1:19 methanol/methylene chloride to 1:6 methanol/methylene chloride) to afford 6-chloro-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine as a yellow-green solid: 1H NMR (400 MHz, DMSO-d6.) d 9.12 (s, 1H), 8.30 (d, J=2.0 Hz, 1H), 8.26 (d, J=2.0 Hz, 1H), 7.99 (d, J=2.8 Hz, 1H), 7.89 (d, J=0.8 Hz, 1H), 7.55 (d, J=0.8 Hz, 1H), 7.43 (dd, J=8.8, 2.8 Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 3.11-3.10 (m, 4H), 2.50-2.49 (m, 4H, merged with DMSO peak), 2.38-2.37 (m, 2H), 1.04 (t, J=7.2 Hz, 3H).

Statistics shows that 1018505-59-3 is playing an increasingly important role. we look forward to future research findings about 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine.

Reference:
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 75806-86-9

Example 2: 2-Bromo-5-chloro-pyridin-3-ylamine; [00382] 2-Bromo-5-chloro-3-nitro-pyridine (11.87 g, 50 mmol) was dissolved in 100 mL ether. Tin(ll) chloride dihydrate (56.4g, 0.5 mol) was dissolved in 100 mL of concentrated hydrochloric acid and added drop wise over 15 minutes to the stirring ethereal solution of the nitro compound. The exothermic reaction brought the ether to boiling and it was allowed to evaporate off. After the addition was complete the reaction mixture was placed on a 50 C oil bath and stirred for 30 minutes to boil of the remaining ether. The flask was then cooled on in an ice bath. The precipitate formed was collected and by filtration and dissolved in 100 mL of water. The pH was adjusted to 9-10 by the addition of concentrated ammonium hydroxide solution and the product was extracted with ethyl acetate (2 x 100 mL). The organic layer was washed with diluted ammonium hydroxide, water and brine and dried over Na2SU4 and the solvent was evaporated to afford 7.4 g of tan crystalline solid. MS m/z : 208.9 (M+H).

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955372-86-8 ,Some common heterocyclic compound, 955372-86-8, molecular formula is C6H3BrFNO2, 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.

I ntermediate 7: 3-Bromo-5-( 2-ftuoro-phenylamino)-isonicotinic acid; Lithium bis(trimethylsilyl)amide (54.6 ml_, 1.0 M in THF, 54.6 mmol) was added to a solution of 2-fluoro aniline (3.5 mL, 36.4 mmol) in THF (100 ml_) at -78 0C. The resulting solution was for 1 h at -780C. S-Bromo-delta-fluoro-isonicotinic acid (1) (4.0 g, 18.2 mmol) was added as a solid, and the reaction solution was stirred for 48 h at room temperature. The reaction solution was concentrated via rotary evaporation; diluted with satd. NaHCO3, and washed with EtOAc. The aqueous solution was acidified with concentrated HCI. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to afford the desired product (4.2 g, 74%) as a yellow solid.

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. 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59105-50-9, (5-Bromopyridin-3-yl)(phenyl)methanone, 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, Formula: C12H8BrNO, blongs to pyridine-derivatives compound. Formula: C12H8BrNO

PdCl2(PPh3)2 (148 mg, 0.21 mmol) and CuI (120.6 mg, 0.63 mmol) were added to asolution of (5-bromopyridin-3-yl)(phenyl)methanone (1.1 g, 4.22 mmol) in Et3N (10 mL)under N2, and the resulting mixture was stirred for 30 min. Then ethynylbenzene (516 mg, 5.1mmol) was added dropwise and the reaction mixture was stirred overnight at roomtemperature, followed by filtration over Celite and evaporation under vacuum. Purificationby column chromatography on silica gel afforded the desired product.To the crude product in a mixture of THF (12 mL) and MeOH (12 mL) was added 10% Pdon carbon (80 mg), and the atmosphere was changed to H2 (2.5 bar). The resulting mixturewas stirred in a Parr hydrogenation apparatus overnight at room temperature, followed byfiltration over Celite and evaporation under vacuum. Purification by column chromatographyon silica gel afforded the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59105-50-9, (5-Bromopyridin-3-yl)(phenyl)methanone, and friends who are interested can also refer to it.

Reference:
Article; Fu, Yun; Sun, Jian; Molecules; vol. 24; 3; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem