Tag: M.W:200-300

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.15862-33-6, name is 3-Bromo-2-hydroxy-5-nitropyridine, molecular formula is C5H3BrN2O3, molecular weight is 218.99, as common compound, the synthetic route is as follows.SDS of cas: 15862-33-6

Under ice-cooling, to a solid mixture of 3-bromo-5-nitro-2-ol (21.4 mmol) and quinoline (10.7Mmol) was slowly added dropwise phosphorus oxychloride (27.8 mmol). The mixture was stirred at 120 C for 3.5 hours, cooled to to 100 C, was added 10 ml of water. The reaction was stirred vigorously in an ice water bath for 1 hour. The precipitate was collected by filtration, washed with water, and dried to give 4.15 g of the title compound. 1H-NMR (CD30D) S9.09 (lH, d, J = 2.4Hz), 8.40 (lH, d, J = 2.4Etazeta).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-33-6, 3-Bromo-2-hydroxy-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICALGROUP CO LTD; Beijing Centaurus Biopharma Technology Co., Ltd.; XIAO, DENGMING; LIANG, ZHI; HU, YUANDONG; HU, QUAN; ZHANG, QINGHUI; HAN, YONGXIN; WANG, HUAN; PENG, YONG; KONG, FANSHENG; LUO, HONG; (60 pag.)CN103130792; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 588729-99-1, 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 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: The 2-chloro-3-amino-5-bromo pyridine (500 mg, 2 . 46mmol) was dissolved in THF (10 ml), added LiHMDS (7.4 ml, 7 . 4mmol), stirring for ten minutes, then adding 4-fluorobenzenesulfonyl chloride (1.44g, 7 . 4mmol), stir at room temperature overnight. By adding dichloromethane (20 ml) dilution, washed with saturated sodium bicarbonate, with dichloromethane (4×30 ml) extraction, combined organic phase, dried, concentrated, the residue column chromatography (petroleum ether: ethyl acetate = 20:1) shall be N-(5-bromo-2-chloro-pyridine-3-yl) – 4-fluorobenzene sulfonaide (770 mg, 87%).

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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; Shanghai Huilun Life Sciences & Technology Co., Ltd.; Cheng, Jianjun; Qin, Jihong; (61 pag.)CN103936762; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944896-42-8 , The common heterocyclic compound, 944896-42-8, name is 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, 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-bromoimidazo[l,2-a]pyridine-3-carboxylic acid (50 mg, 0.21 mmol) in DMF (0.5 mL) was added 3-methoxybenzylamine (37 mg, 0.27 mmol) and HATU (95 mg, 0.25 mmol). The resulting mixture was stirred at room temperature overnight. After removal of solvent by rotary evaporation, the residue was dissolved in ethyl acetate (15 mL) and washed with a saturated aqueous Na2C03 solution (2 x 10 mL), and brine (10 mL), dried over Na2S04, and filtered. The solvent was removed in vacuo and the crude amide product was purified by flash chromatography on silica gel to afford the title compound (52 mg, 70%). LC-MS: single peak at 254 nm, MH+ calcd. for C16H15BrN302: 360, obtained: 360.

The synthetic route of 944896-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, the common compound, a new synthetic route is introduced below. Formula: C7H3ClF3NO2

Example 187 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-3-chloro-5-(trifluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method Z, Example 186 above, but using 3-chloro-5-(trifluoromethyl)-2-pyridine carboxylic acid (Bionet Research). MS m/z=517.1 [M+H]+. Calculated for C19H13ClF8N4O2: 516.77 1H NMR (300 MHz, CHLOROFORM-d) delta=9.82 (br. s., 1H), 8.77 (s, 1H), 8.22-8.08 (m, 2H), 7.10-7.00 (m, 1H), 4.37 (br. s., 2H), 4.04 (dd, J=5.3, 9.7 Hz, 1H), 2.86-2.70 (m, 1H), 1.91 (t, J=13.2 Hz, 1H), 1.64 (s, 3H)

The synthetic route of 80194-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid. A new synthetic method of this compound is introduced below.

5-Bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example Apollo Scientific) was suspended in DCM (100 mL) and then oxalyl chloride (16.98 mL, 194 mmol) was added, followed by DMF (5.01 mL, 64.6 mmol) and the mixture was stirred for 18 h at rt. The solvent was evaporated in vacuo and the residue was redissolved in DCM (100 mL) and evaporated to dryness to give 5-bromo-2-methoxynicotinoyl chloride (16.33 g, 65.2 mmol, 101 % yield) which was used in the next step immediately. (0454) *H NMR (400 MHz, CDCI3) delta ppm 8.49 (d, J=2.7 Hz, 1 H) 8.44 (d, J=2.4 Hz, 1 H) 4.06 (s, 3 (0455) H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54916-66-4, 5-Bromo-2-methoxynicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen, John; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; HAYHOW, Thomas, George, Christopher; LINDON, Matthew, J.; PRESTON, Alexander, G.; SEAL, Jonathan, Thomas; WALL, Ian, David; WATSON, Robert, J.; WOOLVEN, James, Michael; (91 pag.)WO2017/60180; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5470-17-7 , The common heterocyclic compound, 5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, 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.

Step 1: 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N-dimethylethanamine (Intermediatell).To a stirred solution of S-bromo-l-chloro-S-nitropyridine (2.5 g, 10.53 mmol) and 2-(dimethylamino) ethanol (1.877 g, 21.06 mmol) in DMF (10 mL) was added portion wise potassium carbonate (2.91 g, 21.06 mmol) and the mixture was stirred at 60 0C for 2- 3 hrs. Reaction mixture was cooled to RT, diluted with ethyl acetate (50-7OmI), washed with water and then brine, organic layer was collected, dried over sodium sulfate and concentrated in vacuo to give crude 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N- dimethylethanamine (2.70 g, 88 %) as brown liquid. The crude material was taken for next step without further purification. MS (ES+): 292 for C9H12BrN3O3

The synthetic route of 5470-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 885588-12-5, Adding some certain compound to certain chemical reactions, such as: 885588-12-5, name is 2-Bromo-5-fluoro-4-pyridinecarboxylic acid,molecular formula is C6H3BrFNO2, 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 885588-12-5.

To a solution of 2-bromo-5-fluoroisonicotinic acid (3.0 g, 13.64 mmol) in EtOH (30 mL) was added EtONa (3.7 g, 54.55 mmol). The reaction was heated at 60 00 for 24 hours then cooled to room temperature and thionyl chloride (3.2 g, 27.28 mmol) added dropwise. Thereaction was stirred at room temperature overnight then the solvent removed. The residue was partitioned between DOM (20 mL) and water (10 mL) and the aqueous phase extracted with DOM (3 x 10 mL). The combined organic extracts were washed with a saturated aqueous NaHCO3 solution (3 x 10 mL), brine (3 x 10 mL), dried (Na2SO4), filtered and concentrated. The residue obtained was purified by column chromatography(EtOAc/petroleum ether=1/20 v/v) to give the title compound (2.1 g, 56%) as an off-white solid. 1H-NMR (400MHz, ODd3) 6 8.14 (s, 1 H), 7.69 (s, 1 H), 4.40-4.35 (q, J = 7.2 Hz, 2H), 4.21-4.15 (q, J= 6.8 Hz, 2H), 1.46 (t, J= 7.2 Hz, 3H), 1.38 (t, J= 7.2 Hz, 3H); LOMS RT2.61 mm; m/z 274, 276 [M+H].

According to the analysis of related databases, 885588-12-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; BERGMAN, Ylva Elisabet; CAMERINO, Michelle Ang; STUPPLE, Paul Anthony; (81 pag.)WO2017/153520; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59281-14-0, 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.59281-14-0, name is 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, molecular formula is C13H13NO3, molecular weight is 231.25, as common compound, the synthetic route is as follows.

General procedure: 20 mmol of compound 4 (4a-4f) was weighed into 100 mL of dichloromethane, Then add 0.16 mol of manganese dioxide, The mixed system was heated under reflux at 50 C in a oil bath for 72-96 h, and the TLC spot plate was used to detect the reaction process. After the reaction is over, The manganese dioxide was removed by suction filtration and the solvent 5 was evaporated to give compound 5.

Statistics shows that 59281-14-0 is playing an increasingly important role. we look forward to future research findings about 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one.

Reference:
Patent; Zhejiang Gongshang University; Zhou Tao; Shao Lele; (12 pag.)CN106986819; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 207799-10-8, 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. 207799-10-8, name is tert-Butyl (4-bromopyridin-2-yl)carbamate, molecular formula is C10H13BrN2O2, 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.

tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of ter/-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0C is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 muL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO combined organic phases are dried over Na2SO4 and purified by column chromatography (70% EtOAc in heptane) to give the title compound. Yield: 240 mg (76%). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).

According to the analysis of related databases, 207799-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; CURIS, INC.; WO2008/57469; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 162102-79-6, 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 162102-79-6 as follows.

To a solution of dimethyl 4-bromopyridine-2,6-dicarboxylate (CAS 162102-79-6) (2.40 g, 8.8 mmol, 1.0 eq) in MeOH/DCM solution (10/1, 88 mL) was added KOH (896 mg, 8.0 mmol, 0.9 eq) at rt. The reaction mixture was stirred at rt for 3 h and Et20 (80 mL) was added thereto. The resulting white solid was filtered and then redissolved in water (50 mL). 2 M HC1 solution (8 mL) was added. The mixture extracted with DCM (2 x 50 mL). The combined organic layers were washed with brine and dried over anhydrous Na2S04. After removing the solvent, the residue as brown solid was used directly in the next step without further purification (1.0 g, Y: 44%). ESI-MS (M+H) +: 259.9. 1H NMR (400 MHz, CDC13) delta: 8.56 (d, J = 1.7 Hz, 1H), 8.50 (d, J = 1.7 Hz, 1H), 4.04 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,162102-79-6, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; CHAN, Timothy; GUCKIAN, Kevin; JENKINS, Tracy; THOMAS, Jermaine; VESSELS, Jeffery; KUMARAVEL, Gnanasambandam; MEISSNER, Robert; LYSSIKATOS, Joseph; LUCAS, Brian; LEAF, Irina; DUFFIELD, Jeremy; (518 pag.)WO2016/11390; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem