Pyridine-derivatives

Reference of 1227573-02-5, 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.1227573-02-5, name is 3-Bromo-5-fluoroisonicotinaldehyde, molecular formula is C6H3BrFNO, molecular weight is 204, as common compound, the synthetic route is as follows.

Step 2: 3-fluoro-5-(1-oxo-1 ,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde (35b) To 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (210 mg, 0.809 mmol) in DMF (4 mL) was added 3-bromo-5-fluoro-pyridine-4-carbaldehyde (150 mg, 0.735 mmol) and 2M aqueous sodium carbonate (0.735 mL, 1.471 mmol). The reaction mixture was flushed and evacuated with N2 twice followed by the addition of PdCI2(dppf).CH2CI2 adduct (30.0 mg, 0.037 mmol). The reaction mixture was stirred at 100 C for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with water twice. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford 3-fluoro-5-(1 -oxo-1 ,3-dihydro-isobenzofuran-5-yl)-pyridine-4-carbaldehyde, which was taken into the next step without further purification.

Statistics shows that 1227573-02-5 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-fluoroisonicotinaldehyde.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17282-01-8, 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. 17282-01-8, name is 3-Bromo-2-fluoro-5-picoline, molecular formula is C6H5BrFN, 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.

To a solution of B9.1 (300 mg, 1.596 mmol) in THF(10 mL) at -78 oC was added LDA (2 M, 0.8 mL) and the mixture was stirred at -78 oC for 2 h. The mixture was quenched by10 mL H2O and extracted with EtOAc (10 mL x 3). The combined organic phase was concentrated to give the crude product, which was purified by flash chromatography (Normal phase, silica gel, PE_EtOAc=0-100%, UV254 & UV280) to give the title compound (130 mg , 43%) as a yellow oil. 1H-NMR (400 MHz, CDCl3) delta ppm 2.37 (s, 3H), 7.19 (d, 1H), 8.05 (s, 1H).

According to the analysis of related databases, 17282-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884495-01-6 ,Some common heterocyclic compound, 884495-01-6, molecular formula is C5H3BrFNO, 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.

4-Bromo-2-ethoxy-5-fluoropyridine 2.08 mL (26.0 mmol) Ethyliodide and 1.08 g (3.91 mmol) Ag2CO3 are added to a mixture of 500 mg (2.160 mmol) 4-bromo-5-fluoro-pyridin-2-ol in 10 mL DCM. The mixture is stirred at r.t. over night. Then the reaction mixture is quenched by the addition of water and DCM. After filtration the org. layer is separated, dried with Na2SO4 and the solvent is removed in vacuo. C7H7BrFNO (M=220.0 g/mol) ESI-MS: 220 [M+H]+Rt (HPLC): 1.27 min (method X)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-01-6, its application will become more common.

Reference:
Patent; FLECK, Martin; NOSSE, Bernd; HEINE, Niklas; ROTH, Gerald Juergen; US2013/158004; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 90145-48-5, 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. 90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, 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.

Example 5 Preparation of 5-bromo-N-(1-(4-chlorophenylamino)-2-(naphthalen-1-yl)-2- oxoethvDpicolinamide (Compound-1) [0095] A mixture of 5-bronnopicolinannide 111 (0.588 g, 2.92 mmol) and 2,2- dihydroxy-1 -(naphthalen-1 -yl)ethanone 112 (1.20 g, 5.67 mmol) in dioxane (20 ml_) were heated at 100 0C for 18 hours. The dioxane was removed under vacuum and the residue was dissolved in chloroform and methanol and concentrated onto silica gel. The material was purified by auto flash system (CH2CI2 to 1 % MeOH: CH2CI2) to give 5- bromo-N-(1-hydroxy-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide 113 as a tan solid (0.74 g, 66%). [0096] 5-bromo-N-(1 -hydroxy-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide 113(0.74 g, 1.93 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.43 g, 1.96 mmol). The mixture was heated to 50 0C for 30 minutes and cooled to 0 0C. 4-Chloroaniline 114 (0.512 g, 4.01 mmol) in THF (10 ml_) was added and allowed to react for 1 hour. The reaction was quenched with water and the product was extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and concentrated onto silica gel. The product was purified by auto flash column chromatography (30 to 50% CH2CI2: hexane) followed by titration with diethyl ether to give 5-bromo-N-(1-(4- chlorophenylamino)-2-(naphthalen-1 -yl)-2-oxoethyl)picolinamide (Compound-1 , 352 mg, 37%). 1H NMR (300 MHz, CDCI3): delta = 8.83 (d, J = 8.7 Hz, 1 H), 8.50 (d, J = 1.5 Hz, 1 H), 8.46 (d, J = 9.6 Hz, 1 H), 8.39 (dd, J = 1.2, 7.2 Hz, 1 H), 8.07-8.03 (m, 2H), 7.93 (dd, J = 2.4, 8.7 Hz, 1 H), 7.89 (d, J = 7.5 Hz, 1 H), 7.68-7.63 (m, 1 H), 7.56 (t, J = 7.8 Hz, 2H), 7.16 (d, J = 8.7 Hz, 2H), 7.09-7.03 (m, 1 H), 6.82 (d, J = 9.0 Hz, 2H) 5.41 (d, J = 8.1 Hz, 1 H).

According to the analysis of related databases, 90145-48-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 696-42-4, 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.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.

To a stirred solution of 5-fluoropyridine-3-carbonitrile (2.0 g, 16.38 mmol) in methanol (20 mL) at RT was added NaOMe (88mg, 1.64 mmol) and the reaction stirred at RT overnight. Ammonium chloride (1 .40g, 26.21 mmol) was added in a single portion and the reaction mixture stirred overnight at RT. The reaction mixture was filtered and the filtrate concentrated to dryness under reduced pressure. The residue was suspended in EtOH (50 ml_) and then heated at reflux. The undissolved solid was filtered off and the filtrate concentrated to 1/3 of its volume and then left to stand at RT. The resultant crystals were filtered off, washed with EtOH and air-dried to give the desired product (2.1 1 g, 73%) as white crystals. 1H NMR (400 MHz, d6-DMSO) delta 8.93 (d, 1 H), 8.88 (s, 1 H), 8.29-8.23 (m, 1 H).

The chemical industry reduces the impact on the environment during synthesis 696-42-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WAILES, Jeffrey, Steven; BRIGGS, Emma; CARTER, Neil, Brian; MORRIS, Melloney; TATE, Joseph, Andrew; (55 pag.)WO2019/57720; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 562825-95-0, 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 562825-95-0 as follows.

A mixture consisting of ethyl (3-nitropyridin-4-yl) amine (11.76 g, 70 mmol) in acetic acid (140 ml) with sodium acetate (28.7 g, 350 mmol) and bromine (13.44 g, 84 mmol) was stirred in a sealed flask at 100 oc for 18 h. Most of the solvent was removed in vacuo and the residue partitioned between CH2CI2 and water and the aqueous layer basified with NaHCO3. The organic extract was washed with water then brine, dried (Na2SO4) and all volatiles removed in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate: hexane (2: 8) to afford the title compound (10.4 g, 60%). MS: (M+H) + = m/z 246.; A mixture of ethyl (3-nitropyridin-4-yl) amine (11.8 g, 70.0 mmol), acetic acid (140 mL), sodium acetate (28.7 g, 0.35 mol) and bromine (13.4 g, 84.0 mmol) was stirred in a pressure vessel at 100 C for 18 h. The solvent was removed in vacuo and the residue partitioned between CH2CI2 and water. The aqueous layer was made basic (pH No. 8) with NaHCO3 and further extracted with CH2CI2. The combined organic extracts were washed with water, brine and dried (Na2SO4). The solvent was removed in vacuo. and the residue subjected to flash chromatography (20% EtOAc/hexanes, silica gel) to give 10.4 g (60%) of the desired compound. MS (ES+) m/z 246 (M+H) +.; To a solution of the product of 14 (a) (3. 0g, 17. 9mmol) in acetic acid (40ml) was added bromine (3.12g, 1ml, 19. 7mmol) and the mixture was heated at 100C for 20 hours. After cooling the solvent was removed in vacuo and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase was washed with water (x3), dried and evaporated in vacuo. Purification of the residue by silica gel chromatography eluting with 50% dichloromethane in ethyl acetate afforded the title compound (1.9g, 43%).’H NMR (DMSO-d6) 8.73 (1H, s), 8.52 (1H, s), 7.0 (1H, br), 3.25 (2H, m), 1.16 (3H, t, J 7.2Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,562825-95-0, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1190862-70-4, Adding some certain compound to certain chemical reactions, such as: 1190862-70-4, name is Ethyl 5-bromo-6-methylnicotinate,molecular formula is C9H10BrNO2, 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 1190862-70-4.

17C: A mixture of 1A (250 mg, 0.605 mmol), bis(pinacolato)diboron (192 mg,0.756 mmol), potassium acetate (178 mg, 1.815 mmol) and PdC12(dppf)-CH2C12 adduct (24.70 mg, 0.030 mmol) in dioxane (6 mL) was heated at 100 C for 60 mm. After cooling to rt, ethyl 5-bromo-6-methylnicotinate (150 mg, 0.615 mmol) and1,1 ?-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (20.03 mg, 0.031 mmol) were added. The reaction mixture was degassed by nitrogen sparge for 5 mm. 2M K3P04 (aq) (0.922 mL, 1.844 mmol) was quickly added and the reaction mixture heated at 100 C for 15 mm. After cooling to rt, volatiles were removed in vacuo. The cmde residue was purified with column chromatography on the Isco system (40 g, 0-100%EtOAc/Hex to afford 17C (300 mg, 0.573 mmol, 93 % yield) as a crystalline beige solid. MS ESI m/z 498.0 (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. 1190862-70-4, Ethyl 5-bromo-6-methylnicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUO, Junqing; HART, Amy, C.; MACOR, John, E.; MERTZMAN, Michael, E.; PITTS, William, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; CHEN, Jie; DZIERBA, Carolyn, Diane; LUO, Guanglin; SHI, Jianliang; SIT, Sing-Yuen; (428 pag.)WO2018/148626; (2018); 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, the common compound, a new synthetic route is introduced below. Application In Synthesis of N-((6-Chloropyridin-3-yl)methyl)ethanamine

To prepare compound 4e a solution of 4d (1 mmol) and N-((6-chloropyridin-3-yl)methyl)ethanamine (0.187 g, 1.1 mmol) in acetonitrile (4 mL) was heated under reflux. The progress of the reaction was monitored by TLC. After completion, the cooled mixture was filtered and the precipitate was washed with cold acetonitrile (4 mL) to afford the desired product 4e.

The synthetic route of 120739-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Nanyang; Xia, Shanshan; Zou, Minming; Shao, Xusheng; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5293 – 5300;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 863704-60-3 ,Some common heterocyclic compound, 863704-60-3, molecular formula is C12H8FNO2, 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.

B) 6-(4-Fluorophenyl)picolinic acid-N-oxide A mixture of picolinic acid derivative (1.0 g,, 4.6 mmol), Na2HPO4 (1.2 g) and mCPBA (1.1 g, ~70% from Aldrich) in CH2ClCH2Cl (30 mL) was stirred at rt for 2 h. Additional Na2HPO4 (0.8 g) and mCPBA (1.0 g, ~70% from Aldrich) was added to the reaction mixture and it was stirred for 3 h at rt. Another Na2HPO4 (0.5 g) and mCPBA (0.5 g, ~70% from Aldrich) was added to the reaction mixture and it was stirred at rt overnight. Next morning CHCl3 (160 mL) and 2N aq HCl (50 mL) were added to the reation mixture, the organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by flash column on silica gel eluding with EtOAc/MeOH/HOAc//700:240:60 to obtain the desired product contaminated by mCPBA. This impure material was purified by preparative HPLC to obtain the desired product (175 mg, 16%) as a white solid. 1H NMR (DMF-d7) 8.45 dd, 1H, J=8.3, 2.2 Hz), 8.15 (d, 1H, J=2.2 Hz), 8.13-8.00 (mn, 4H), 7.45 (t, 2H, 8.7 Hz).

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. 863704-60-3, 6-(4-Fluorophenyl)picolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/60613; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine. A new synthetic method of this compound is introduced below.

General procedure: Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem