Category: pyridine-derivatives

Electric Literature of 89488-30-2 ,Some common heterocyclic compound, 89488-30-2, molecular formula is C6H6BrNO, 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-Bromo-1,3-dimethyl-1H-pyridin-2-one B-1 To a suspension of 5-bromo-2-hydroxy-3-methyl pyridine A1 (1.000 g; 5.053 mmol) and potassium carbonate (1.397 g; 10.105 mmol) in DMF (5.000 ml) is carefully added iodomethane (0.346 ml; 5.558 mmol). The reaction mixture is stirred overnight (16 h) at room temperature. The reaction mixture is then quenched with 10% ammonia solution (10 ml) and 30 ml water is added. It is extracted with 3*50 ml EtOAc. The combined organic layer is dried with Na2SO4, filtered and concentrated under reduced pressure to afford the product. Yield: 98% (1.0 g; 4.95 mmol) HPLC-MS: (M+H)+=202/204; tRet=0.65 min; method LCMS BAS1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89488-30-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; MARTIN, Laetitia; SMETHURST, Christian; US2015/51208; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3678-62-4, 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.3678-62-4, name is 2-Chloro-4-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.

lOg of 1.-.2-Ghlar6-4-methylpyridine are ”dissolved in 50 ml.’of ‘-CH3CN.’ and- heated to’?? 85C. Then a mixture of 32g -N-“Chlorosuccinimid and l,6g”AIBN is added over a period of 5 minutes. -The resulting- mixture is refluxed . for two?hours,- -then the solvent is removed in vacuo, the residue treated ? with 100ml of CH2C12 ?? and washed with water 2.’times.”The organic phases ‘are collected, dried over Na2S04 and the residue obtained after evaporation of the solvent-is- distilled (80C, 100 mTorr) . Yield 79%

The chemical industry reduces the impact on the environment during synthesis 3678-62-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10642; (2006); 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. 92138-35-7, name is 6-Chloro-3-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloro-3-nitropyridin-2(1H)-one

Intermediate 63-Aminopyridin-2(l//)-one hydrochlorideTo a stirred solution of 6-chloro-3-nitropyridin-2(lH)-one (Intermediate 5, 3.5 g, 20 mmol) in ethyl acetate (50 mL) was added SnCl2.H2O(32 g, 142 mmol) in portions over a period of 15 min at room temperature, then the mixture was re fluxed at 80 0C for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and neutralized with solid NaHCO3 (50 g). The mixture was filtered and the solids were washed with ethyl acetate (2 x 50 mL). The filtrate was concentrated to remove ethyl acetate under vacuum and the residue was taken in ice cold dioxane (20 mL). 4N HCl in dioxane (10 mL) was added and the mixture was concentrated to give desired product in 95%yield (3.5 g, 19 mmol).MS (ES): 143.2 (M-I) for C5H5ClN2O1H-NMR (CDCl3, 300 MHz): delta 4.20 (br s, 2H), 6.20 (d, J= 7.6 Hz, IH), 6.59 (d, J= 7.6 Hz,IH).

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, 92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27732; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 351227-42-4, Adding some certain compound to certain chemical reactions, such as: 351227-42-4, name is 6-Chloro-4-iodopyridin-3-amine,molecular formula is C5H4ClIN2, 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 351227-42-4.

Route B : A mixture of 6-chloro-4-iodopyridin-3-ylamine (Preparation 8, 0.33g, 1.30mmol), pyruvic acid (0.27mL, 3.89mmol), DABCO (0.44g, 3.89mmol) and palladium acetate (0.015g, 0.07mmol) in dry DMF was stirred vigorously and degassed with argon for 15min. The reaction mixture was heated to 1070C for 5h. The reaction mixture was allowed to cool to rt and stirred for 16h. The volatiles were removed under reduced pressure and the residue partitioned between EtOAc (10OmL) and water (5OmL). The layers were separated and the aqueous extracted with EtOAc (2x50mL). The combined organics were extracted with aqueous NaOH (2M, 3x70mL). The combined aqueous extracts were acidified to pH 4 by careful addition of glacial acetic acid, then extracted with EtOAc (3x60mL). The combined organics were washed with brine (5OmL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a brown solid. RT=2.72min, m/z (ES+) =197 [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. 351227-42-4, 6-Chloro-4-iodopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1000341-55-8, 6-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine, 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, SDS of cas: 1000341-55-8, blongs to pyridine-derivatives compound. SDS of cas: 1000341-55-8

Into a 100 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was added a solution of 6-chloro-3-iodo-lH-pyrrolo[3,2-c]pyridine (1.70 g, 6.10 mmol) in N,N-dimethylformamide (20.0 mL) followed by sodium hydride (600 mg, 25.0 mmol). This was followed by addition of 2-iodopropane (2.20 g, 12.9 mmol) dropwise with stirring at 0 C. The reaction mixture was stirred for 16 h at room temperature. The reaction was then quenched by addition of water (50mL). The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers were separated and combined. The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 :7) to afford the title compound (1.40 g, 72.0 %) as a yellow solid. LCMS (ESI): RT (min) = 1.549, [M+H]+ = 321, method = M.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1000341-55-8, 6-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 914942-88-4, 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. 914942-88-4, name is tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate, molecular formula is C13H18IN5O2, 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.

Al.12 (0.3g, 0.74 mm ol), pyruvic acid (98mg, 1.12mmol), triethylamine and palladium dibenzylidene acetone (68mg, 0.074mmol) in dry DMF (3mL) were heated to 120C for 15 min in a microwave. The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (10 niL). The organic extract was discarded and the aqueous layer acidified to pH 3-4 using IN HCL The acidified aqueous layer was then extracted with ethyl acetate (3 x 20 mL), the combined organics dried (MgSO4) and evaporated in vacuo to give A168.1 (lbetalmg, 62%). HPLC YMC S-5 4.6x33mm EPO W(2min grad): retention time 1.32min, M+H+ = 346.31, NMR (400MHz, DMSO) delta 12.49 (s, IH), 8.16 (s, IH), 7.47 (s, IH), 4.04 (s, 3H), 3.29 (s, 3H), 1.30 (s, 9H).

According to the analysis of related databases, 914942-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 790692-90-9, 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. 790692-90-9, name is 6-Chloro-5-iodo-3-nitropyridin-2-amine. A new synthetic method of this compound is introduced below.

The compound 268-100 was prepared as follows. To a solution of 6-chloro-3-nitropyridin-2-amine (630 mg, 3.63 mmol) in ethanol (11 mL) was add I2 (920 mg, 3.62 mmol) and Ag2SO4 (1132 mg, 3.63 mmol).). The resulting solution was stirred overnight at room temperature and dissolved in water (100 mL), then extracted with ethyl acetate (3×80 ml). The combined organic layers were washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated under vacuum to produce 6-chloro-5-iodo-3-nitropyridin-2-amine as a yellow solid (640 mg, 59%). Next, to a solution of 6-chloro-5-iodo-3-nitropyridin-2-amine (640 mg, 2.14 mmol) in ethanol (40 ml) and water (10 ml) was added Fe powder (1.93 g, 34.46 mmol) and NH4Cl (887 mg, 16.58 mmol). The resulting solution was heated to reflux for 4 h and then concentrated. The residue was dissolved in water (100 mL) and extracted with ethyl acetate (3×80 ml). The combined organic layers was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 33% ethyl acetate in petroleum ether to produce 6-chloro-5-iodopyridine-2,3-diamine as a brown solid (560 mg, 97%). The mixture of 6-chloro-5-iodopyridine-2,3-diamine (100 mg, 0.37 mmol), (2,3-dichlorophenyl)boronic acid (147.3 mg, 0.77 mmol), Pd(Ph3P)4 (42.9 mg, 0.04 mmol) and sodium carbonate (118.2 mg, 1.12 mmol) in water (5 mL) and dioxane (15 mL) was heated to reflux overnight. Then the resulting solution was quenched with water (100 mL) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine as a brown solid (80 mg, 75%). Finally, the solution of 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine (80 mg, 0.28 mmol) in trifluoroacetic acid (10 mL) and hydrochloric acid (conc., 2 mL) was heated to reflux overnight. Then the resulting mixture was quenched with water (100 mL), adjusted pH to 8 with sodium carbonate and extracted with ethyl acetate (3×80 mL). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,3-dichlorophenyl)-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine. Trifluoroacetic acid as a off-white solid (2 mg, 2%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,790692-90-9, its application will become more common.

Reference:
Patent; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 182181-42-6, 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.182181-42-6, name is 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine, molecular formula is C9H9ClN2, molecular weight is 180.63, as common compound, the synthetic route is as follows.

EXAMPLE 55 2-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine monomaleic acid salt. Refer to Chart E A mixture of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine (Example 54, Step 1; 0.294 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.396 g) diisopropylethylamine (0.35 mL), and THF (2 mL) is heated at 75 C. for 5 hours. The mixture is then concentrated under reduced pressure, partitioned between saturated aq. sodium bicarbonate and dichloromethane, and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated to give 2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine.

Statistics shows that 182181-42-6 is playing an increasingly important role. we look forward to future research findings about 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine.

Reference:
Patent; Pharmacia & Upjohn Company; US5912246; (1999); A;,
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. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate, molecular formula is C8H8BrNO2, 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. Computed Properties of C8H8BrNO2

Step 1 To a solution of 5-bromo-4-methylpyridine-2-carboxylic acid methyl ester (2.207 g, 9.59 mmol), 4-methoxylphenylboronic acid (1.604 g, 10.55 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.313 g, 0.480 mmol) in THF (30 mL) was added potassium carbonate (2.0 M in water, 10.1 mL, 20.15 mmol). The mixture was purged with nitrogen and heated at 50 C. for 1 hour and at 60 C. for 5 hours. The reaction was poured into ethyl acetate and was washed with brine, dried over sodium sulfate, filtered and concentrated. It was purified by column chromatography to yield methyl 5-(4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.47 g, 9.59 mmol) as a pink solid. MS ESI calc’d. for C15H16NO3 [M+H]+ 258.1. found 258.1.

With the rapid development of chemical substances, we look forward to future research findings about 886365-06-6.

Reference:
Patent; Shao, Pengcheng Patrick; Sun, Wanying; Katipally, Revathi Reddy; Vachal, Petr; Ye, Feng; Liu, Jian; Sha, Deyou; US2013/109649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13269-19-7, 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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

General procedure: choloro acetylcholoride (24mmol) and Et3N (24mmol) was added to a solution of 2-chloro-3-aminopyridine 7e (20mmol) in CH2Cl2 (20mL) at room temperature. The mixture was stirred for 5 hrs, and the solvent was evaporated under vacuum. The residue was purified by column chromatography (CH2Cl2:CH3OH: 30:1) on silica gel to obtain pure compound 8e as a white powder in 72% yield. To a solution of amide derivative 8e (5mmol) and potassium carbonate (7.5mmol) in acetonitrile (20ml) was added isothiocyanate (6mmol) during about 5min. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under vacuum. The residue was extracted with ethyl acetate (20mL×3). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The obtained residue was purified by silica gel flash chromatography column (CH2Cl2:CH3OH: 30:1) to afford 5l as a white solid in 82% yield. To a solution of 5l (1mmol) in glacial acetic acid (5mL) were added aldehyde 6b (1mmol) and beta-alanine (1mmol). The resulting mixture was stirred under reflux for 2h. Upon completion of the reaction, the mixture was cooled, the reaction was quenched with water, and the precipitate was filtered off, then the residue was purified by column chromatography (CH2Cl2:CH3OH: 15:1) on silica gel to obtain pure compound 2r as a faint yellow powder in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13269-19-7, its application will become more common.

Reference:
Article; Cai, Ming-Guang; Wu, Yang; Chang, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2517 – 2520;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem