Month: April 2022

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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

Stage b)1H-Pyrazolo[3,4-b]pyridine-3-carbonitrile; 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (500 mg, 2.67 mmol) is heated in 33% strength aqueous ammonia solution (10 ml) in a microwave at 140 C. for 10 min. The mixture is then concentrated in vacuo, and the residue is stirred with 100 ml of ethyl acetate and 20 ml of tert-butyl methyl ether at 70 C. Insoluble constituents are removed by suction filtration while hot, and the filtrate is concentrated. Drying results in 346 mg (90% of theory) of the title compound as pale beige crystals.1H-NMR (400 MHz, DMSO-d6): delta=7.47 (dd, J=8.2, 4.5 Hz, 1H), 8.46 (dd, J=8.2, 1.5 Hz, 1H), 8.73 (dd, J=4.5, 1.5 Hz, 1H), 15.02 (br. s, 1H).LC/MS (method 1): Rt=1.30 min.; MS (ESIpos): m/z=145 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 956010-87-0.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/113507; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Product Details of 98273-79-1

INTERMEDIATE 22Methyl 3-(3′-ethoxy-3-fluorobiphenyl-4-ylamino)isonicotinate; A mixture of methyl 3-chloroisonicotinate (1.00 g, 5.83 mmol), intermediate 1 (1.35 g, 5.83 mmol), Cs2CO3(2.66 g, 8.16 mmol) and Xantphos (0.68 g, 1.17 mmol) in dioxane (20 mL) was stirred under argon atmosphere for 10 min. Then Pd2(dba)3 (0.53 g, 0.58 mmol) was added and the mixture stirred under argon atmosphere at 12O0C overnight. The reaction mixture was filtered over Celite and washed with CH2CI2. The filtrate was concentrated and purified by column chromatography eluting with EtOAc/hexane/Et3N (20/79/1) and the desired compound was obtained. Yield=51% LRMS: m/z 367 (M+1 )+.1H NMR (250 MHz1 CDCI3) delta ppm: 9.26 (s, 1 H); 8.8 (s, 1H); 8.25 (d, J = 5.3 Hz, 1 H); 7.87 (d, J = 5.3 Hz, 1 H); 7.72-7.45 (m, 4H); 7.3 (d, J = 8.2 Hz, 1 H); 7.26 (s, 1H); 7.05 (dd, J = 8.2, J= 1.8 Hz, 1 H); 4.25 (c, J = 7 Hz, 2H); 4.12 (s, 3H); 1.61 (t, J = 7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 127446-34-8 ,Some common heterocyclic compound, 127446-34-8, molecular formula is C11H13ClN2O2, 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.

10.i. 7-chloro-3-fluoro-1,8-naphthyridin-2(1H)-one To a solution of N-(6-chloro-3-formylpyridin-2-yl)pivalamide (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 mL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between 1N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (100 mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6N HCl (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 0 C. and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+H+] for C8H4N2OClF.

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. 127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109306-86-7, 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.109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.

Example 20The boronic acid compound D was synthesized as described below. That is, 2-(2-bromophenyl)pyridine (J. Am. Chem. Soc., 2006, vol. 128, p. 6,790 and 6,791.) (4.0 mmol) was added in a flask of 50 mL filled with dry nitrogen together with toluene (6.4 mL) and tetrahydrofuran (1.6 mL) as a solvent and was cooled to -78 C. After a 1.5-M hexane solution of butyl lithium (3.1 mL, 4.8 mmol) was added to this solution dropwise, and the mixture was stirred at -78 C. for 30 minutes. To the reaction mixture was added triisopropyl borate (4.8 mL), and the mixture was stirred at room temperature for 19 hours. After the reaction mixture was concentrated under reduced pressure, the residue was purified by column chromatography (alumina, ethyl acetate-methanol=5:1), so that methyl ester of the boronic acid compound D was obtained. After this product was dissolved in a mixture of water and methanol, the solvent was removed at 50 C. to 60 C. under reduced pressure, so that the boronic acid compound D was obtained (669 mg, yield: 84%). The structure of the boronic acid compound D was identified by 1H NMR and 13C NMR. 1H NMR (CD3OD) delta 7.42 (dt, J=1.5, 7.5 Hz, 1H), 7.47 (dt, J=1.5, 7.5 Hz, 1H), 7.60 (ddd, J=0.9, 1.5, 7.5 Hz, 1H), 7.64 (ddd, J=1.5, 5.7, 7.5 Hz, 1H), 7.96 (ddd, J=1.2, 1.5, 7.5 Hz, 1H), 8.18 (ddd, J=1.2, 1.5, 8.1 Hz, 1H), 8.27 (ddd, J=1.5, 7.5, 8.1 Hz, 1H), 8.49 (ddd, J=0.9, 1.5, 5.7 Hz, 1H); 13C NMR (CD3OD) delta 119.3, 123.2, 125.0, 129.5, 131.7, 132.3, 138.9, 143.1, 144.7, 157.1.

The chemical industry reduces the impact on the environment during synthesis 109306-86-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY; US2011/319620; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 280566-45-2 ,Some common heterocyclic compound, 280566-45-2, molecular formula is C7H3ClF3NO2, 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.

Intermediate 242-Amino-6-(trifluoromethyl)nicotinic acidA solution of 2-chloro-6-(trifluoromethyl)nicotinic acid (1.87 g, 8.29 mmol) in (2,4- dimethoxyphenyl)methanamine (2.491 ml, 16.58 mmol) was heated to 100 0C overnight. The reaction mixture was concentrated under vacuum and partitioned between water and DCM. Evaporation of the organic layer provided a dark brown residue, which was dissolved in TFA (2.55 ml, 33.16 mmol), and the resulting mixture was stirred for 30 minutes. The precipitate formed was discarded via filtration and concentration of the filtrate under reduced pressure gave a residue. This residue was dissolved in HCl (IN, 200 mL) and the aqueous solution was washed with Et2O and evaporated under reduced pressure to give a solid. This solid was washed with DCM/Hexanes, dried in a vacuum oven overnight and characterized as the title product (2 g). LCMS: 207.0 [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. 280566-45-2, 2-Chloro-6-(trifluoromethyl)nicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 103058-87-3, Adding some certain compound to certain chemical reactions, such as: 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde,molecular formula is C7H6BrNO2, 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 103058-87-3.

EXAMPLE 7 To a solution of 6.5 g of 5-bromo-2-methoxypyridine-3-carboxaldehyde in 30 ml of tetrahydrofuran under nitrogen was added 200 ml of methanol followed by 4.6 g of 4-chloroacetophenone. Then, a solution of 6.6 g of 85% potassium hydroxide in 15 ml of water was added. The mixture warmed, became yellow, and deposited a thick precipitate. It was then stirred mechanically for about 1.5 hours until the temperature fell back to about 25 C. It was then further cooled in an ice bath and neutralized by the addition of 20 ml of aqueous 5M hydrochloric aid in small portions. The resulting pasty mixture was poured into 400 ml of water, acidified to a pH of 1 with aqueous 1N hydrochloric acid and then filtered. The moist product was boiled with 2-propanol/ethyl acetate (3:1), cooled and filtered. The filter cake was dried under reduced pressure to give (E)-3-(5-bromo-2-methoxy-3-pyridinyl)-1-(4-chlorophenyl)-2-propen-1-one as a pale yellow solid melting at about 168.5-171.5 C.

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. 103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merrell Dow Pharmaceuticals Inc.; US4588733; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67367-24-2, 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. 67367-24-2, name is Methyl 4-hydroxynicotinate, molecular formula is C7H7NO3, 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.

Step 2 Methyl 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) nicotinate (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimeth yl-8-dihydromethylene-1H-naphtho[2,1-d][1,3]dioxin (300.00 mg, 729.20 umol) was dissolved in N,N-dimethylformamide (5.00 mL), and potassium carbonate (201.57 mg, 1.46 mmol) and methyl 4-hydroxynicotate (223.34 mg, 1.46 mmol) were added successively and then stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction was quenched by adding 30 mL water and then extracted with ethyl acetate (30.00 mL). The organic phase was successively washed with water (30 mL) and saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by column chromatography (silica, petroleum ether/ethyl acetate=1/1) to give methyl 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy) nicotinate (a yellow oil, 200 mg, yield: 56.71%). 1H NMR (400 MHz, CDCl3) 8.89 (s, 1H), 8.51 (d, J=6.0 Hz, 1H), 6.80 (d, J=5.8 Hz, 1H), 4.88 (s, 1H), 4.66-4.50 (m, 2H), 4.24-4.14 (m, 1H), 4.03 (d, J=11.3 Hz, 1H), 3.98-3.85 (m, 4H), 3.54-3.39 (m, 2H), 2.42 (d, J=12.3 Hz, 1H), 2.27 (dq, J=3.0, 13.2 Hz, 1H), 2.16-2.04 (m, 2H), 1.95-1.87 (m, 3H), 1.83-1.76 (m, 1H), 1.72-1.67 (m, 3H), 1.54 (td, J=7.4, 19.3 Hz, 4H), 1.49-1.38 (m, 3H), 1.36 (s, 3H), 1.30-1.24 (m, 3H), 0.79 (s, 3H).

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 67367-24-2, Methyl 4-hydroxynicotinate.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, 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, 639091-75-1, blongs to pyridine-derivatives compound. Formula: C12H16N2O4

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaC12 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight atambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaC1 (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,639091-75-1, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174064; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 917391-98-1, 5-Fluoro-2-oxo-1,2-dihydropyridine-3-carbaldehyde, 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, Recommanded Product: 917391-98-1, blongs to pyridine-derivatives compound. Recommanded Product: 917391-98-1

(b) 1 -Ethyl-5- fluoro-2-oxo-pyridine-3-carbaldehvde K2Ctheta3 (0.830 g, 6.00 mmol) was added to a solution of 5-Fluoro-2-oxo-pyridine- 3-carbaldehyde (0.424, 3.00 mmol) in dry DME (10 mL). Ethyl iodide (0.303 mL, 3.75 mmol) was added dropwise while the reaction was heated to reflux. After 8 hours the reaction was cooled to RT, filtered and evaporated. Purification using flash chromatography (heptane/EtOAc, 10-100%) gave 0.249 g (49 %) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,917391-98-1, 5-Fluoro-2-oxo-1,2-dihydropyridine-3-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/135323; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256810-26-0, Adding some certain compound to certain chemical reactions, such as: 1256810-26-0, name is 6-Bromo-3-methoxypicolinic acid,molecular formula is C7H6BrNO3, 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 1256810-26-0.

To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3- methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. -NMR (DMSO-i, 400 MHz) delta 8.98 (t, J = 6.0 Hz, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.58 (d, J = 8.8 Hz, 1H), 7.39-7.43 (m, 2H), 7.33 (d, J = 8.4 Hz, 2H), 4.22 (d, J = 6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355 / 357.

According to the analysis of related databases, 1256810-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem