Category: pyridine-derivatives

Electric Literature of 15862-50-7, Adding some certain compound to certain chemical reactions, such as: 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine,molecular formula is C6H5BrN2O3, 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 15862-50-7.

Step 1) A mixture of 3-bromo-2-methoxy-5-nitropyridine (Intermediate 51, 25 g, 107.3 mmol), tributyl(l-ethoxyvinyl)stannane (43.5 mL, 130.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (8.68 g, 7.51 mmol) in anhydrous DMAC (100 mL) was purged with N2 for 30 min and then heated at 120C for 3 h. After cooling to rt the mixture was poured into 1M aqueous HC1 (500 mL). The mixture was stirred overnight before saturated aqueous potassium sodium tartrate solution (800 mL) was added and the mixture was extracted with EtOAc (2 x 300 mL). The combined organic phases were dried (MgS04), filtered and concentrated in vacuo. Purification by gradient flash column chromatography eluting with 0-30% EtOAc in z’sohexane yielded a yellow solid, which was slurried in diethyl ether and filtered to afford l-(2-methoxy-5-nitropyridin-3-yl)ethanone (3.38 g, 17.2 mmol) as white solid. LCMS (Method 3): m/z 197 (ES+), at 1.09 min. (0387) 1H NMR: (400 MHz, DMSO-i) delta: 2.62 (s, 3H), 4.13 (s, 3H), 8.66 (d, J=2.8, 1H), 9.24 (d, J=2.8, 1H).

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. 15862-50-7, 3-Bromo-2-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HEPTARES THERAPEUTICS LIMITED; CHRISTOPHER, John Andrew; BUCKNELL, Sarah Joanne; CONGREVE, Miles Stuart; TEHAN, Benjamin Gerald; NONOO, Rebecca Helen; BROWN, Giles Albert; SWAIN, Nigel Alan; MILLS, Mark; (111 pag.)WO2019/86902; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1124-29-4, 5-Acetylpyridin-2(1H)-one, 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, Computed Properties of C7H7NO2, blongs to pyridine-derivatives compound. Computed Properties of C7H7NO2

To a suspension of 5-acetylpyridin-2(lH)-one (500 mg, 3.6 mmol) in pyridine (4 mL) was added 0-(4-methoxybenzyl)hydroxylamine hydrochloride (761 mg, 4.0 mmol) and the reaction mixture was stirred at RT for 18 h. The mixture was then partitioned between CH2CI2 (10 mL) and 0 (10 mL), the organic layer was washed with 0 (2 x 10 mL), brine (2 x 10 mL), dried with Na2S04, filtered and concentrated under reduced pressure. The residue was triturated with toluene to give the title compound as a white solid (991 mg, 99%) MS (ES+) C15H16N2O3requires: 272, found: 273 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1124-29-4, 5-Acetylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; MARSZALEK, Joe; LIU, Gang; KANG, Zhijun; CARROLL, Christopher, L.; MCAFOOS, Timothy; CZAKO, Barbara; WO2014/31928; (2014); A2;,
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. 128071-77-2, name is 4-Bromo-2-fluoronicotinaldehyde, molecular formula is C6H3BrFNO, 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. Formula: C6H3BrFNO

A mixture of 4-bromo-2-fluoro- pyridine-3-carbaldehyde (2.04 g, 10.0 mmol, 1.0 eq.), methylhydrazine (1.05 mL, 20.0 mmol, 2.0 eq.) and DIEA (3.48 mL, 20.0 mmol, 2.0 eq.) in MeCN (50 mL, 0.2 M) was stirred at 50 C. After 1 h, the mixture was diluted with EtOAc and washed with water (2x). The aqueous layer was extracted with EtOAc (3x). The combined extracts were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (0-60% EtOAc/hexanes) afforded the title compound as a white crystalline solid (1.73 g, 82%). XH NMR (400 MHz, CDCI3) delta 8.36 (d, J= 4.9 Hz, 1H), 8.04 (s, 1H), 7.33 (d, J = 4.9 Hz, 1H), 4.18 (s, 3H); ES-MS [M+l]+: 214.2.

With the rapid development of chemical substances, we look forward to future research findings about 128071-77-2.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P., Jeffrey; BOLLINGER, Katrina A.; ENGERS, Darren W.; BLOBAUM, Anna L.; ENGERS, Julie L.; ROOK, Jerri M.; (96 pag.)WO2018/63552; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67310-56-9 , The common heterocyclic compound, 67310-56-9, name is 1-(5-Hydroxypyridin-2-yl)ethanone, molecular formula is C7H7NO2, 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.

K2CO3 (504 mg, 3.65 mmol) followed benzylbromide (0.22 mL, 1.82 mmol) was added to a solution of 1-(5-hydroxypyridin-2-yl)ethanone (250 mg, 1.82 mmol) in MeCN (8 mL) at rt. The mixture was stirred at rt overnight and filtered. The filtrate was concentrated and the residue purified by chromatography to give the sub-title compound (360 mg, 1.58 mmol, 87 %).

The synthetic route of 67310-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ATROGI AB; PELCMAN, Benjamin; BENGTSSON, Tore; (93 pag.)WO2019/53427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 727356-19-6, 2-Bromo-6-(chloromethyl)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, name: 2-Bromo-6-(chloromethyl)pyridine, blongs to pyridine-derivatives compound. name: 2-Bromo-6-(chloromethyl)pyridine

A214.1a (133 mmol) was dissolved in DMF (250 niL) and potassium phthalimide (54.2 g, 293 mmol) was added portionwise to maintain the internal temperature below 3O0C. An additional portion of DMF (50 mL) was used to rinse the flask and powder funnel used for the potassium phthalimide addition. The reaction was stirred at room temperature overnight after which the reaction was judged complete by HPLC analysis. Water (600 mL) was added slowly to the reaction and after 30 minutes of stirring the resulting precipitate was collected by filtration, washed with several portions of water (1000 mL total) and allowed to air dry. The resulting solid, which contained the desired product along with excess phthalimide, was resuspended in water (700 mL) and the solution was made basic by addition of 1 N NaOH (3 mL). After slurrying for 20 minutes the solids were collected by filtration, washed with several portions of water and allowed to air dry. The solid still contained some phthalimide so was resuspended in MeOH (50 mL) and water (800 mL) and allowed to stir vigorously for 2 days. The solid was again collected by filtration, then slurried in hot MeOH (200-300 mL), cooled to room temperature and filtered. The solid was air dried to afford the phthalimide adduct, A214.1, along with residual phthalimide as a white solid. This material was used without further purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, and friends who are interested can also refer to it.

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

Electric Literature of 60010-03-9, Adding some certain compound to certain chemical reactions, such as: 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine,molecular formula is C6H4Cl2N2O2, 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 60010-03-9.

6-Chloro-4-methyl-3-nitro-2-pyrrolidin-1 -yl-pyridine (Intermediate compound)To a solution of crude 2,6-dichloro-4-methyl-3-nitro-pyridine (see previous reaction; 23.87g; 115mmol), pyrrolidine (11 ml 1.1 eq) in 100 ml_ acetonitrile was added TEA (ca. 50 ml 3eq). After stirring overnight at room temperature one aliquot of water was added to the reaction mixture and the acetonitrile was removed in vacuo. The remaining aqueous layer was extracted with EtOAc (3x15OmL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to yield a dark semi-solid. The crude material was purified by flash column chromatography (5-40% EtOAc in heptane) to yield 1 Og (26% over three steps) of the title compound as a yellow solid.

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. 60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1443-42-1, 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. 1443-42-1, name is (4-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, 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.

General procedure: To a solution of compound 3w (0.70g, 2.1mmol) in THF (10ml) was added phenyltrimethylammonium tribromide (0.79g, 2.1mmol). The reaction mixture was stirred at room temperature for 12h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with water (30mL×2), dried over anhydrous Na2SO4 and concentrated to afford the intermediate 4w. To a solution of different pyridin-3-ylmethanamine derivatives (2.1mmol) in acetone (10ml) was added Et3N (0.43g, 4.2mmol). The reaction mixture was stirred for 5min and was added CS2 (0.24g, 3.15mmol) to continuously stir for 30min. The intermediate 4w were added respectively and this mixture was stirred at room temperature for 4h. Water (50mL) was added and the mixture was extracted with ethyl acetate (10mL×3), the combined organic phase was washed with brine (30mL×2), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to provide the product.

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 1443-42-1, (4-Methylpyridin-3-yl)methanamine.

Reference:
Article; Li, Ridong; Ning, Xianling; Zhou, Shuo; Lin, Zhiqiang; Wu, Xingyu; Chen, Hong; Bai, Xinyu; Wang, Xin; Ge, Zemei; Li, Runtao; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 48 – 65;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 103058-87-3 , The common heterocyclic compound, 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, 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.

n-Butyllithium (120 ml, 1.6M in hexane) is added to a suspension of 80.74 g of (3-methoxy- propyl)triphenylphosphonium bromide [11 1088-69-8] in 250 ml of tetrahydrofuran under an argon atmosphere at 0C. The reaction mixture is stirred at 0C for 50 minutes and then 28 g of 5-bromo-2-methoxypyridine-3-carbaldehyde [103058-87-3] are added. The reaction mixture is stirred at 0C for 1 hour and then at room temperature for 1 hour and diluted with tert-butyl methyl ether. The solution is washed with 1 M sodium bicarbonate solution. The organic phase is dried over sodium sulphate and evaporated. The title compound is obtained as a yellowish oil from the residue by flash chromatography (SiO2 60F). Rt = 5.03 (Gradient I)

The synthetic route of 103058-87-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2007/31558; (2007); 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H2BrClN2O2

A mixture of 2- bromo-5-chloro-3-nitropyridine (1.00 g, 4.21 mmol), methyl 2,2-difluoro-2- (fluorosulfonyl)acetate (0.971 g, 5.05 mmol), and copper(I) iodide (0.963 g, 5.05 mmol) in DMF (10 mL) was heated at 85 oC for 16 h. Upon cooling to rt, the mixture was diluted with ethyl acetate (20 mL) and filtered through Celite. The filtrate was concentrated under vacuum to almost dryness. The residue was diluted with ethyl acetate (180 mL), washed with water (3 x 40 mL) and brine (30 mL), and dried over anhydrous MgSO4. The desired product, 5-chloro-3-nitro-2-(trifluoromethyl)pyridine (0.578 g, 2.55 mmol, 60.6% yield), was isolated as a light yellow oil by flash chromatography (80 g silica gel, solid loading, 5-20% ethyl acetate/hexane).1H NMR (500 MHz, CHLOROFORM-d) delta 8.89 (d, J=2.2 Hz, 1H), 8.25 (d, J=1.7 Hz, 1H).

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JALAGAM, Prasada Rao; NAIR, Satheesh Kesavan; PANDA, Manoranjan; FENG, Jianxin; WANG, Wei; LIU, Chunjian; ELLSWORTH, Bruce A.; SARABU, Ramakanth; SWIDORSKI, Jacob; HARTZ, Richard, A.; XU, Li; YOON, David S.; BENO, Brett R.; REGUEIRO-REN, Alicia; (457 pag.)WO2019/67702; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 185315-53-1, Adding some certain compound to certain chemical reactions, such as: 185315-53-1, name is 3-Chloro-2-(chloromethyl)pyridine,molecular formula is C6H5Cl2N, 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 185315-53-1.

General procedure: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 27; N-[(3S)-l-[5-(tert-Butylamino)-3-[(3-chloropyridin-2-yl)methyl]triazolo[4,5- d]pyrimidin-7 -yl] pyrrolidin- 3 -yl] acetamide; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin- l-yl)-3-[[2- (trifluoromethyl)phenyl] methyl] triazolo [4, 5 -d] pyrimidin- 5 – amine (example 22) the title compound was prepared from N-[(3S)-l-[5-(tert-butylamino)- 3H-triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-yl]acetamide and 3-chloro-2- (chloromethyl)pyridine. MS(m/e): 444.4 (MH+).

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. 185315-53-1, 3-Chloro-2-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem