Category: pyridine-derivatives

Related Products of 65973-52-6, 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 65973-52-6, name is Methyl 4,6-dichloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

[00217] Step B; 4.6-Dichloronicotinic acid:[00218] To a solution of methyl 4,6-dichloronicotinate in a mixture of THF (400 ml), MeOH ( 100 ml) andH2O ( 100 ml) was added a solution of NaOH (10 g) in 40 ml H2O. The mixture was stirred for 40 min. at room temp. Then, the solvents were reduced and it was acidified with cone. HCl to a pH of about 2. It was extracted using a mixture of Et2O/EtOAc and the organic layer was dried with Na2SO4. The solvents were removed and the residue dried in vacuo to obtain the title compound as a white solid (12.3 g, 69%). Rf (CHCl3/MeOH 10:1) = 0.85. 1H-NMR (300 MHz, DMSO-D6): delta = 8.80 (s, 1H), 7.90 (s, 1H).

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 65973-52-6, Methyl 4,6-dichloronicotinate.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 94446-97-6, 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. 94446-97-6, name is 2-Bromo-3-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

This intermediate was generated by a modified procedure based on that disclosed in Viswanathan, R., et al., J. Am.Chem. Soc., 125, 163 (2003) and Synthesis 2, 330 (2005). A three neck round bottom flask with a stir bar was chargedwith I-5 (40.1 g, 135.7 mmol), I-7 (8.2 g, 13.6 mmol), powdered KOH (69.1 g, 1221.4 mmol), and DCM (600 ml).The opaque yellow suspension was cooled to -78C and the flask fitted with a dropping funnel. A suspension of I-4 (152.0 g, 610.7 mmol) in 400 ml DCM was transferred to the dropping funnel and added to the reaction at -78C over about 1 hr. The suspension in the dropping funnel would occasionally settle and the solid would be resuspended. After the end of the addition the funnel was rinsed with an additional 200 ml of DCM and the rinse was added to the reaction. After 10 hrs at -78C. the reaction was allowed to stir overnight as it warmed to room temperature. Analysis of the reaction by HPLC and TLC showed complete conversion of I-4. The reaction was diluted with 3 L of DCM transferred to a 15 L reactor and extracted 2 x 1 L of water. During the separation the organic phase appeared cloudy due to a solid formed from I-4. The organic phase was collected then washed with NaCl (satd.aqueous), dried over anhydrous sodium sulphate, filtered and concentrated to near dryness and purified by normal phase flash chromatography. A three solvent mobile phase was used for the separation; initially DCM/hexanes to elute the excess I-4, followed by EtOAc/Hexanes to elute the title compound (S)-tert-butyl 3-(2-bromopyridin-3-yl)-2-((diphenylmethylene)amino)propanoate (I-8) obtained as a yellow solid (23.1 g, 226.0 mmol, 37%). H1 NMR (400 MHz, CDCl3) delta 8.20(1H, dd, J=4.2 Hz), 7.60(2H, d, J=8 Hz), 7.56(1H, dd,J=4.2 Hz), 7.45-7.25(6H, m), 7.12(1H, dd, J=8.4 Hz), 6.67(1H, d, J=d Hz), 4.39(1H, dd, J=8.4 Hz), 3.39(1H, dd,J=12.4 Hz), 3.21(1H, dd, J=12.4 Hz), 1.46(9H, s), MS(LC/MS) m/z observed 464.87, expected 465.12 [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,94446-97-6, its application will become more common.

Reference:
Patent; viDA Therapeutics Inc.; Cameron, Dale R.; (36 pag.)US9458192; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915107-30-1, 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. 915107-30-1, name is Methyl 6-chloro-5-hydroxynicotinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 6-chloro-5-hydroxypyridine-3-carboxylate (720 mg, 3.84 mmol) in DMF (10 mL) was added methyl iodide (635 mg, 4.46 mmol) at room temperature. The resulting solution was stirred for 8 h at room temperature and diluted with water (30 mL). The mixture was extracted with ethyl acetate (50 mL*3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was concentrated under reduced pressure to yield methyl 6-chloro-5-methoxypyridine-3-carboxylate as yellow solid (600 mg, 66%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,915107-30-1, Methyl 6-chloro-5-hydroxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 152684-30-5 ,Some common heterocyclic compound, 152684-30-5, molecular formula is C6H5BrN2O3, 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.

AL 2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-L3,2-dioxaborolan-2-yl)pyridine; To a dry flask was added 5-bromo-2-methoxy-3-nitropyridine (1.3 g, 5.0 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.6 g, 6.4 mmol), and Pd(dppf)Cl2 (0.2 g, 0.25 mmol). Potassium acetate (1.5 g, 15 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (30 mL) was added and the reaction was heated at 80 0C in an oil bath overnight. The reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting material was purified by silica gel chromatography (eluting with 0-50% ethyl acetate in hexane) to yield the product (0.2 g, 15%). ESI-MS m/z calc. 280.12, found 199.1 (MW[-C6Hio]+l)+. Retention time 0.7 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,152684-30-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/141119; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 920979-04-0, 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. 920979-04-0, name is 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4F3IN2, 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.

10.2 (5-Trifluoromethyl)pyrrolo[3,2-b]pyridine-2-carboxylic acid; 0.5 g (1.74 mmol) of 3-amino-2-iodo-6-(trifluoromethyl)pyridine, obtained in Stage 10.1, 0.45 g (5.21 mmol) of pyruvic acid, 0.51 mL (5.21 mmol) of 1,4-diazabicyclo[2.2.2]octane and 10 mL of dry dimethylformamide are introduced, under argon, into a sealed tube. The solution is degassed for some minutes, then 0.19 g (0.87 mmol) of palladium acetate is added, the tube is closed and it is refluxed at 130 C. for 4 hours. The cooled solution is then concentrated at reduced pressure and the residue is taken up in 100 mL of ethyl acetate. The organic phase is extracted successively with 2×50 mL of an aqueous solution of 2N sodium hydroxide. The basic aqueous phases are combined, cooled to 0 C., acidified with additions of hydrochloric acid and then extracted with 4×50 mL of ethyl acetate. These organic phases are combined, washed with 20 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. We obtain 0.22 g of product, which is used as it is in the next stage.

According to the analysis of related databases, 920979-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2010/41634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

NMP (7 mL) was added to a round bottom, placed under nitrogen and cooled to 00C. NaH (1.16 g, 29.1 mmol) was added portionwise followed by the addition of methyl cyanoacetate (1.31 ml, 14.5 mmol) (in 3 mL of NMP) dropwise. After stirring for 30 minutes at 00C, 2- bromo-3,5-dichloropyridine (3.0 g, 13.2 mmol) was added and the reaction was heated to 1300C for 5 hours. The reaction was allowed to cool, poured into ice and extracted twice with ethyl acetate. The ethyl acetate was combined, dried over MgSO4, filtered and concentrated. The amorphous material was crystallized from methanol to afford the desired compound (700 mg, 2.86 mmol, 21.6 % yield) as light brown needles.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58539-77-8, 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. 58539-77-8, name is 3-(Chloromethyl)-2-methylpyridine hydrochloride. A new synthetic method of this compound is introduced below.

A mixture of the compound of Example 42 (0.20 g, 0.57 [MMOL),] cesium carbonate (2.0 g, 5.7 [MMOL)] and 3-chloromethyl-2-methyl-pyridine hydrochloride (0.16 g, 0.91 [MMOL)] in a 2: 1 THF/DMF mixture was heated at [80C] for 15 hours. The cooled mixture was filtered and concentrated, and then water (30 mL) was added and the mixture extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with brine, dried [(MGS04),] filtered and concentrated to a foam (0.31 [G).] The residue was purified by flash chromatography using a 30% to 70% ethyl acetate/hexanes eluant to afford 122 mg (47%) of the title compound as an oil. Mass spectrum: (m/e) 458 (M++1, +ion).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-77-8, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/5229; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 717843-48-6, 3-Bromo-6-methylpicolinonitrile, 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, HPLC of Formula: C7H5BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5BrN2

(3) the 2 – bromo -6 – methyl -2 – cyano pyridine (25g, 127mmol) dissolved in the 1L in concentrated hydrochloric acid (HCl), mixture in 110 C stirring reaction under the condition of 2 days; removing the solvent to obtain crude product; the obtained crude product is dissolved in water, and addingNaHCO3, then filtered; the filtrate is ethyl acetate extraction, Na2SO4drying and vacuum concentrated to get the crude product 3 – bromo -6 – methyl -2 – picolinic acid; two product adds up the yield of 69.3%, about 19g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717843-48-6, 3-Bromo-6-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Jianxiong Vocational and Technical College; Gu, Zhun; Wang, Yang; Jin, Chen; (7 pag.)CN106045902; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73290-22-9, 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.73290-22-9, name is 2-Bromo-5-iodopyridine, molecular formula is C5H3BrIN, molecular weight is 283.89, as common compound, the synthetic route is as follows.

To a solution of 2-bromo-5-iodopyridine (15 g, 52.8 mmol) in dry THF (300 mL) at -78C was added n-BuLi (2.5 M, 21 mL), and stirred at -78 C for 1 hrs, followed by addition of tert-butyl 3-oxopiperidine-1-carboxylate (10.5 g, 52.8 mmol) in THF. The reaction mixture was stirred at -78 C–6O C for 2 hrs, quenched by NH4C1/H20 and extracted by EA. The organic was dried to give a residue, which was purified by flash chromatography to afford the titlecompound (8.4 g, 45%). MS (ES+) C15HnBrN2O3 requires: 356, found: 357 [M+H].

The chemical industry reduces the impact on the environment during synthesis 73290-22-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BROOIJMANS, Natasja; BRUBAKER, Jason, D.; FLEMING, Paul, E.; HODOUS, Brian, L.; KIM, Joseph, L.; WAETZIG, Josh; WILLIAMS, Brett; WILSON, Douglas; WILSON, Kevin, J.; (347 pag.)WO2017/181117; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52313-50-5, Adding some certain compound to certain chemical reactions, such as: 52313-50-5, name is Picolinimidamide,molecular formula is C6H7N3, 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 52313-50-5.

A solution of 1-(2,4-difluorophenyl)piperidin-4-one (0.24 g, 1.14 mmol) and DMFDMA (0.5 mL) in acetonitrile (5 ml) was heated with stuffing at 90 C for 2 hrs. The mixture was concentrated in vacuo and the residue was dissolved in EtOH (lOmL). To the solution was addedpyridine-2-carboxamidine (91 mg, 0.75 mmol) and potassium carbonate (210 mg, L50 mmol) successively. After being heated at 90 C overnight, the resulting mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (20 mL) for three times. The organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-(2,4-difluorophenyl)-2-(2-pyridyl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine (6 mg). ?H NMR (400MHz, DMSO-d6): oe 8.77 (s, 1H), 8.74 (d, 1H),8.36 (d, 1H), 7.97 (dt, 1H), 7.52 (ddd, 1H), 7.34 – 7.16 (m, 2H), 7.14 – 6.97 (m, 1H), 4.33 (s, 2H),3.48 (t, 2H), 3.10 (t, 2H). MS obsd. (ESIj [(M+H)]: 325.

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. 52313-50-5, Picolinimidamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem