Tag: M.W:200-300

Synthetic Route of 1033610-45-5, 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. 1033610-45-5, name is 4-Bromo-3,5-dimethoxypyridine. A new synthetic method of this compound is introduced below.

To an ice-cooled suspension of sodium hydride (60% dispersion in mineral oil, 650 mg, 16.3 mmol) in dry DMF (10 ml) was added 4-methoxybenzyl alcohol (2.24 g, 16.3 mmol) drop-wise via syringe. Vigorous evolution of hydrogen was observed and the reaction was allowed to warm to room temperature and stirred for 15 minutes. 4-Bromo-3,5-dimethoxypyridine (1.17 g, 5.41 mmol) was added and the reaction heated to 900C overnight. After cooling, only trace starting material could be detected by TLC analysis and the reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water 3 times then brine, dried over MgSO4 and concentrated onto silica-gel under reduced pressure. The solid residue was purified by flash chromatography (silica-gel, eluted sequentially with EtOAc : hexanes, 2:1, 1:0) to give the product as a tan solid (865 mg, 58%). 1H-NMR (300 MHz, CDCl3) delta 7.96 (s, 2H), 7.33 (d, J= 8.5 Hz, 2H), 6.84 (d, J= 8.5 Hz, 2H), 5.11 (s, 2H), 3.89 (s, 6H), 3.78 (s, 3H). MS (ES+) m/z 276.1 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033610-45-5, 4-Bromo-3,5-dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BIONOMICS LIMITED; WO2008/70908; (2008); 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 885326-88-5, name is Methyl 6-amino-4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 6-amino-4-bromopicolinate

A mixture of Example 106C (644 mg, 2.79 mmol, 1 eq), 2- chloroacetaldehyde (40 % in H20, 1.63 mL, 23.33 eq) and NaHC03 (398 mg, 4.74 mmol, 1.7 eq) in EtOH (10 mL) was heated to 80 C 12 hours. The mixture was cooled to 20 C and basified with aq. Na2C03. The aqueous phase was extracted with ethyl acetate (30 mL*2). The combined organic phase was washed with brine (10 mL*2), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (gradient 5 to 50% EA in PE). Example 106D (600 mg crude) was obtained as a brown oil and used directly in next step.

With the rapid development of chemical substances, we look forward to future research findings about 885326-88-5.

Reference:
Patent; CHRYSALIS, INC.; GWALTNEY, Stephen; (147 pag.)WO2017/214413; (2017); 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. 78427-26-6, name is 1-(4-Aminophenyl)pyridin-1-ium chloride, the common compound, a new synthetic route is introduced below. Recommanded Product: 1-(4-Aminophenyl)pyridin-1-ium chloride

To a 250 mL Erlenmeyer flask were added 14.6 g of l-(4-aminophenyl)pyridine-l-ium chloride (“PyCI”), 20 g deionized ice water, and 80 g of deionized water under stirring. After all PyCI solids were dissolved, 40 mL of 2M sodium nitrite was added to this solution, which was then put into an ice-water bath and cooled to [0062] In a separate 2L vessel, 22.89 g of N-(5-chloro-2-methoxyphenyl)-3-hydroxy-2-naphthamide (available from TCI as Naphthol AS-CA) was dissolved in a solution 37.5 mL of 2M NaOH and 250 ml of ethanol. The resulting solution was cooled to 5C. To this solution was added the diazo-PyCI solution dropwise with vigorous stirring over a time period of 40 min to 1 hour. Since the solution became very viscous during the addition period, another 200 mL of ethanol and 300 mL of methanol were added to ensure a good mixing. During the whole addition period, approximately 50 mL of 2M NaOH was added to the reaction mixture to maintain a pH > 12. The reaction mixture was allowed to warm back to room temperature gradually and then stirred at room temperature overnight. The resulting red precipitate was removed by filtration, washed with deionized water, and dried in the vacuum oven at 60C to yield 32.4 g of the Cationic Synergist I.

The synthetic route of 78427-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cabot Corporation; Xu, Jinqi; (21 pag.)CN106062087; (2016); A;,
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 1093879-46-9, name is 2-(6-Bromopyridin-2-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H6BrNO2

Into a mixture of 2-(6-bromopyridin-2-yl)acetic acid (54 mg, 0.24 mmol) and (2S,4R)-N-(2′-chloro-2-fluoro-[l, -biphenyl]-3-yl)-4-fluoropyrrolidine-2-carboxamide hydrochloride (91 mg, 0.24 mmol) in DMF (2 mL), TBTU (116 mg, 0.36 mmol) was added followed by DIEA (0.083 mL, 0.48 mmol) with stirring. After the reaction was finished, NaHCO3 solution (10 mL) was added and the resulting solid precipitation was collected by filtration, washed with water, and purified by silica gel column chromatography to afford (2S,4R)- 1 -(2-(6-bromopyridin-2-yl)acetyl)-N-(2′-chloro-2-fluoro-[ 1 , 1 ‘-biphenyl]-3 -yl)-4- fluoropyrrolidine-2-carboxamide (124 mg) (41).1H NMR (400 MHz, Chloroform-d) delta 9.33 – 9.18 (m, 1H), 8.21 (ddd, J = 1.7, 7.3, 8.7 Hz, 1H), 7.53 – 7.42 (m, 2H), 7.31 (dddd, J = 4.1, 7.3, 9.6, 12.7 Hz, 6H), 7.14 (td, J = 1.1, 8.0 Hz, 1H), 7.01 (ddd, J = 1.7, 6.8, 7.8 Hz, 1H), 5.30 (d, J = 53.0 Hz, 1H), 4.95 (dd, J = 7.1, 8.4 Hz, 1H), 4.13 (ddt, J = 1.7, 12.6, 19.7 Hz, 1H), 3.92 (d, J = 2.0 Hz, 2H), 3.67 (ddd, J = 3.5, 12.6, 33.0 Hz, 1H), 2.86 – 2.71 (m, 1H), 2.45 (dddt, J = 2.0, 8.4, 14.8, 21.8 Hz, 1H). LC (method A): =3.08 min. LC/MS (EI) mlz: [M + H]+ 534.

With the rapid development of chemical substances, we look forward to future research findings about 1093879-46-9.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6945-67-1, 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 6945-67-1, name is 2-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of sodium (480mg, 21mmol) dissolved in 1-propanol (45mL), was added 2-bromo-4-nitropyridine [(3.2g, 19.2mmol), J. Med. Chem. 46(7), 1273-1276; 2003] and the mixture was heated at 95C for 2 hours. The solvent was then evaporated under reduced pressure and the residue was suspended in chloroform and filtered. The filtrate was washed with water, dried over magnesium sulfate, and concentrated in vacuo to give an oily residue. The residue was distilled and title product was obtained during a temperature range of 145-150C, as a solid in 58% yield, 2.67g. 1H-NMR(CDCl3, 400MHz) delta: 0.70(t, 3H), 1.58(m, 2H), 3.95(t, 2H), 6.65(m, 1H), 6.83(d, 1H), 8.02(d, 1H) Micro analysis found (%); C(44.10), H(4.70), N(6.80); C8H10BrNO requires (%); C(44.50), H(4.70), N(6.50)

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 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; Pfizer Limited; EP1595881; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1018505-59-3, 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 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

The 4 – (2 – dimethyl carbonyl -2 – carbonyl – ethylamine) -2 – pyrimidine formic acid (1.26 g 1.2 eq), 5 – (4 – ethyl – piperazine -1 – yl) – piperidine -2 – amino (0.81 g 1 eq) and triethylamine (500 mul) in DMF (15 ml) in, then added HBTU (1.51 g 1.5 eq). The mixture stirring at room temperature to 16 hours, then EtOAc (50 ml) and saturated NaHCO3Solution (15 ml), and for separating each layer of EtOAc (2 × 15 ml) extraction the aqueous layer, the combined organic layer drying (MgSO4), Filtering and evaporation to dryness, the residue through the column chromatography purification, and to obtain white solid compound of 1.04 g (yield: 47%).

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 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Zou Mingming; Hu Xiande; Sui Rongchun; Xu Man; (14 pag.)CN108689997; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 117873-72-0, 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 117873-72-0, name is 2,6-Dibromo-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

(1) Production of 2-bromo-4-methoxy-6-{3-(trifluoromethyl)phenoxy} pyridine as an intermediate product 3.34 g (0.187*1.1 mol) of 3-(trifluoromethyl) phenol was dissolved in about 30 ml of dimethyl formamide. The solution was further mixed with 0.78 g (ca. 60% in mineral oil; 0.0187*1.04 mol) of sodium hydride and then with 5.00 g (0.0187 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 120 C. for about 2 hours, the mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed with hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane), and the obtained product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield by weight: 3.23 g; yield by percentage: 50%; solid; melting point: 57 to 60 C.; 1 H-NMR (60 MHz, CDCl3, delta): 3.75 (3H, s), 6.26 (1H, d, J=2 Hz), 6.75 (1H, d, J=2 Hz), 7.0-7.6 (4H, complex).

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 117873-72-0, 2,6-Dibromo-4-methoxypyridine.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6005112; (1999); A;,
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. 6945-67-1, name is 2-Bromo-4-nitropyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-4-nitropyridine

EXAMPLE 47 To a suspension of 2-bromo-4-nitropyridine (406 mg), 3-aminophenylboronic acid (403 mg) and tetrakis(triphenylphosphine)-palladium (116 mg) in 1,2-dimethoxyethane (10 ml) was added 2M aqueous solution of sodium carbonate (2.6 ml). The mixture was stirred at 80 C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give crude 3-(4-nitropyridin-2-yl)aniline. This compound was used for next step without purification.

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, 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 914358-72-8 ,Some common heterocyclic compound, 914358-72-8, molecular formula is C6H5BrClN, 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 60(1r,4r)-6′-(5-Chloro-6-methylpyridin-3-yl)-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (287 mg, 1.13 mmol), (1r,4r)-6′-bromo-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (Example 19, 213 mg, 0.57 mmol) and potassium acetate (167 mg, 1.70 mmol) and dioxane (3 mL) were added and the mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 (32.4 mg, 0.04 mmol) was added and the mixture was heated to reflux for 1.5 h under N2 atmosphere. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (120 mg, 0.47 mmol) was added and the reaction was heated to reflux overnight. The volatiles were removed in vacuo and 80 mg of the residue ((1r,4r)-4-methoxy-5”-methyl-6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (MS (ES+) m/z 424 [M+H]+) was mixed with 5-bromo-3-chloro-2-methylpyridine (Intermediate 43, 47 mg, 0.23 mmol), K2CO3 (0.38 mL, 0.76 mmol) and dioxane (2 mL). The mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 adduct (138 mg, 0.19 mmol) was added. The vial was sealed and heated in a microwave reactor at 140 C. for 30 min. EtOAc was added and the mixture was washed with brine and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (12 g SiO2, 0-20% MeOH containing 0.1 M NH3 in DCM). The crude product was purified with preparative chromatography. The fractions containing product were combined and concentrated. The water phase was extracted with DCM and the phases were separated using a phase separator. The organic phase was concentrated in vacuo yielding the title compound (5 mg, 6% yield): 1H NMR (CD3OD) delta ppm 1.11 (td, 1H), 1.24-1.43 (m, 2H), 1.49 (td, 1H), 1.63 (td, 2H), 1.90-2.00 (m, 2H), 2.32 (s, 3H), 2.61 (s, 3H), 3.04-3.12 (m, 1H), 3.15 (d, 1H), 3.25 (d, 1H), 3.33 (s, 3H), 6.99 (d, 1H), 7.47 (d, 1H), 7.55 (dd, 1H), 7.99 (d, 1 H), 8.51 (d, 1H); MS (MM-ES+APCI)+ m/z 423 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914358-72-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 823221-93-8 ,Some common heterocyclic compound, 823221-93-8, molecular formula is C6H2BrClF3N, 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 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (commercially available) (75 mg, 0.288mmol), 2,2-dimethylpropanamide (32 mg, 0.317 mmol), XantPhos Pd G3 precatalyst (13 mg,0.0 14 mmol), K2C03 (79 mg, 0.57 mmol) in 1 ,4-Dioxane (0.5 mL) was heated at 90C for 0.5hand then 110C for 2h. Purification by reverse phase HPLC delivered product (14 mg, 15%). LC-MS: (positive ES MH+ 281).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823221-93-8, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PHADTE, Mangala; SONAWANE, Ravindra; HENNESSY, Alan Joseph; MORRIS, James Alan; BOEHMER, Jutta Elisabeth; DESSON, Timothy Robert; GOODWIN-TINDALL, Jake; WO2015/59262; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem