Category: pyridine-derivatives

Electric Literature of 22282-96-8, 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 22282-96-8, name is 2-Bromo-6-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 6-bromo-2-methyl-3-nitropyridine (XIV) (250 g, 1.15 mol, 1.00 eq) and NH4C1 (300 g, 5.61 mol, 4.88 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 65C. To this mixture was added Fe (130 g, 2.33 mol, 2.02 eq) and HC1 (15.3 g, 419 mmol, 0.36 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-2-methylpyridin-3-amine (XV) as brown solid (373 g, 1.99 mol, 86.7% yield) which was used for the next step without any purification. ?H NMR (DM50-cl6, 400 MHz) ppm 6.01 (dd, J= 2.3, 7.9 Hz, 2H), 7.03 (d, J= 8.2 Hz, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

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 22282-96-8, 2-Bromo-6-methyl-5-nitropyridine.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72716-80-4, 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 72716-80-4, name is 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 3-cyano-5,6-dimethyl-2-pyridone (1-013-02) (12.0 g) in water (293 mL) was added conc. hydrochloric acid (293 mL), and the reaction mixture was reflux with stirring in oil-bath at 135 C. After 3 days, the reaction mixture was cooled, and evaporated under reduced pressure. To the residue (24.75 g) were added chloroform (300 mL) and methanol (15 mL), and the reaction mixture was heated in a water bath at 65 C, and the dissolble material was filtered off. Furthermore, the dissolble material was treated by chloroform (200 mL) and methanol (10 mL) in a similar manner to described above. The combined filtrates were evaporated under reduced pressure. To the obtained residue (13.26 g) were added methanol (150 mL) and potassium carbonate (10 g). After stirred at room temperature for 30 min, the dissolble material was filtered off. The filtrate was evaporated under reduced pressure. To the obtained residue (14.7 g) was added chloroform (200 mL), and the dissolble material was filtered off again. The filtrate was evaporated under reduced pressure to give 5,6-dimethyl-2-pyridone (1-013-03) (9.41 g, 94.3%, m.p.: 202-207 C)1H NMR (300 MHz, CDCl3): delta 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J = 9.0 Hz, 1H), 7.26 (d,J = 9.0 Hz, 1H), 13.17 (br s, 1H).

According to the analysis of related databases, 72716-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1477186; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, 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 77199-09-8, name is Ethyl 5-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Example 593-(((5-(l-(4-(2,3-Dimethylphenoxy)butanoyl)-l,2,3,4-tetrahydroquinolin-5-yl)pyridin-2- yl)methoxy)carbonylamino)propanoic acid[00204] To a solution of NaBH4 (0.822 g, 21.73 mmol) in MeOH (25 mL) was added ethyl 5-bromopicolinate (1.0 g, 4.35 mmol) portion-wise over a period of 10 min at room temperature. The mixture was stirred at room temperature for 10 min and then heated to 70 C for 30 min. The solvent was removed in vacuo, and the resulting residue was diluted with EtOAc and water. The aqueous phase was adjusted to pH 7 with 1 N aq. HCl, and extracted with EtOAc. The combined organic layer was dried over MgS04, filtered, and concentrated in vacuo to afford the title compound (0.65 g, 80% yield) as a white solid. LCMS, [M+H]+ = 187.9.

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 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ROBL, Jeffrey A.; LI, Jun; KENNEDY, Lawrence J.; WALKER, Steven J.; WANG, Haixia; WASHBURN, William N.; AHMAD, Saleem; NGU, Khehyong; WO2012/149236; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4966-90-9 ,Some common heterocyclic compound, 4966-90-9, molecular formula is C6H6N2O4, 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.

(1)2,4-dichloro-6-methyl-3-nitropyridine 6-methyl-3-nitropyridin-2,4-diol (1.7 g, 10 mmol) was dissolved in 10 mL POCl3, heated to 95C, and stirred for 1.5 h. The excess POCl3 was removed through centrifugation. 100 mL ice water was carefully added. The reaction solution was extracted with ethyl acetate (80 mL*3). The organic phase was combined, washed with saturated brine, dried with anhydrous Na2SO4 and spinned to dryness to afford 1.773 g yellow powder with a yield of 85.7 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4966-90-9, its application will become more common.

Reference:
Patent; Xuanzhu Pharmaco., Ltd.; EP2524917; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256834-13-5 , The common heterocyclic compound, 1256834-13-5, name is 4-Bromo-6-chloronicotinic acid, molecular formula is C6H3BrClNO2, 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.

To a solution of 6-bromo-4-chloronicotinic acid (3 g, 12.69 mmol) in DMF (42 mL) was added HATU (6.27 g, 16.49 mmol), (R)-4-amino-3-fluoro-2-methylbutan-2-ol hydrochloride (2.4 g, 15.23 mmol), and N,N-Diisopropylethylamine (5.62 ml, 32.26 mmol). The resulting solution was stirred at room temperature overnight and subsequently diluted with ethyl acetate. The organic solution was washed with saturated aqueous lithium chloride (3 times), then dried over Na^SCri. and then concentrated. The residue was purified by silica gel chromatography (eluent: EtO Ac/hexanes) to provide (R)-6-bromo-4-chloro-N-(2-fluoro-3-hydroxy-3- methylbutyl)nicotinamide.ES/MS: 341.1 (M+H+).

The synthetic route of 1256834-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AMMANN, Stephen; BACON, Elizabeth M.; BRIZGYS, Gediminas; CHIN, Elbert; CHOU, Chienhung; COTTELL, Jeromy J.; NDUKWE, Marilyn; TAYLOR, James G.; WRIGHT, Nathan E.; YANG, Zheng-Yu; ZIPFEL, Sheila M.; (138 pag.)WO2020/36979; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 112110-07-3, 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

Dissolve the amine obtained in Step 2 (380 mg, 2.35 mmol), pyridine (371 mg, 4.7 mmol) in DCM (8 mL), cool to 0C in ice bath. Add slowly phenyl chloroformate (403 mg, 2.35 mmol). After addition, stir the reaction at 0-5C for 2 hrs. Pour the mixture into water (50 mL), adjust pH to neutral with 1M HC1 solution, extract with EtOAc (15 mLx3). Combine the organic layers; wash with brine (100 mL), dry over anhydrous a2S04, and concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, EtOAc_PE=15:85) affords the target compound (390 mg, 59%).

Statistics shows that 112110-07-3 is playing an increasingly important role. we look forward to future research findings about 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); 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 5444-01-9, name is 4-Methylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5444-01-9

4-methylnicotinamide (7) is prepared starting from the intermediate product (6) by treatment with the ion-exchange resin Amberlite IRA- 410.The resin (400 mg), preconditioned in 10% aqueous NaOH (5 ml) for 90 minutes and washed with degassed water until the excess alkalinity disappears, is added with an aqueous solution of (6) (200 mg; 1.7 mmol), reflux heating for approximately one hour.At the end of this period the solution is filtered and the resin is washed thoroughly with 10 ml of boiling water: on adding the washing water to the filtrate, a solid residue is obtained by lyophilization, consisting in practically pure 4-methylnicotinamide (7) (220 mg; 1.6 mmol; yield 85%; m.p. 160-1610C).

With the rapid development of chemical substances, we look forward to future research findings about 5444-01-9.

Reference:
Patent; UNIVERSITA DEGLI STUDI DI ROMA LA SAPIENZA; WO2008/90585; (2008); A2;,
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. 89167-34-0, name is 4-Chloro-3-iodopyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H3ClIN

Intermediate 20: 4-chloro-N-r2-fluoro-4-(tr)methylsilyl)phenv?pyridin-3-amine; To a solution of 4-chloro-3-iodopyridine (1.37 g, 5.73 mmo.) in dry toluene 25 mL, was added sequentially Pd(OAc)2 (122.5 mg, 0.55 mmol), rac-BINAP (0.34 g, 0.55 mmol), Cs2CO3 (8.9 g, 27.3 mmol), and 2-fluoro-4-(trimethylsilyl)aniline (1 g, 5.45 mmol). The mixture was degassed with nitrogen twice. The mixture was then refluxed at 130 0C under nitrogen for 3 days. The mixture was filtered and the filtrate was diluted with EtOAc, washed with H2O, brine, dried over anhydours Na2SO4. The organic phase76 was concentrated and the resulting residue was purified by flash column with 20% EtOAc-Hexane (0.3% Et3N in Hexane) to afford desired adduct (1.14 g, 70.1%). LC/MS [Method A: rt: 6.14 min; m/z: 295 (M+1)].

The synthetic route of 89167-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
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. 89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, 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. Safety of 3-Iodopyridin-4-ol

General procedure: 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;

With the rapid development of chemical substances, we look forward to future research findings about 89282-03-1.

Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
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 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H6ClNO3

To a solution of the intermediate of step 3 (2.7 g, 14.4 mmol) in CH2Cl2 (75 mL) were added DIPEA (7.53 mL, 43.3 mmol) and HATU (5.49 g, 14.4 mmol) at 0 C. and RM was stirred for 15 min. O,N-Dimethyl-hydroxylamine hydrochloride (1.41 g, 14.4 mmol) was added at 0 C. and the RM was stirred at RT for 14 h. The RM was diluted with CH2Cl2 and was consecutively washed with water, sat. NaHCO3, sat. NH4Cl and brine. The organic layer was dried and the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiO2, EtOAc/Hex) to yield the desired compound (3.1 g, 93%). [0353] LC-MS (Method 3): m/z [M+H]+=231.1 (MW calc.=230.65); Rt=2.61 min.

With the rapid development of chemical substances, we look forward to future research findings about 716362-10-6.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem