Tag: M.W:200-300

Application of 960298-00-4 ,Some common heterocyclic compound, 960298-00-4, molecular formula is C12H10BrNO, 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 2-benzyloxy-4-bromopyridine 6 (201 mg, 0.8 mmol) in MeOH(4.5 mL) was added conc. HCl (2.3 mL). The mixture was heated at reflux overnight.Then the reaction mixture was cooled to room temperature and concentrated underreduced pressure. The residue was poured into cold water and carefully quenchedwith aq. sat. Na2CO3. The aqueous layer was extracted with ethyl acetate (3x). Thecombined organic layers were washed with brine, dried (Na2SO4), filtered andconcentrated under reduced pressure. The crude was purified by flash chromatography on silica gel (EtOAc/MeOH: 98/2) to give 1c (109 mg, 82%) as acolorless solid. Data for 1c are reported above.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,960298-00-4, its application will become more common.

Reference:
Article; Honraedt, Aurelien; Gallagher, Timothy; Synlett; vol. 27; 1; (2016); p. 67 – 69;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61337-89-1, 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. 61337-89-1, name is 2-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanol, molecular formula is C17H21N3O, 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 3 Preparation of mirtazapine (I) from 1-(3-hydroxymethylpyridyl-2)-2-phenyl-4-methylpiperazine 100 ml of concentrated sulfuric acid was cooled to about 15 C. 50 grams (0.18 mole) of 1-(3-hydroxymethylpyridyl-2)-2-phenyl-4-methylpiperazine was added slowly to the sulfuric acid, and the temperature was maintained below 20 C. The temperature was then raised to 30 C., and the reaction mixture was stirred for 12 hours maintaining the temperature between 25 C. to 30 C. The reaction mass was then quenched in 1 liter of ice cold water. The pH of the reaction mixture was adjusted to about 10-11 using 20% to 25% aqueous ammonia solution while maintaining the temperature below 30 C. 500 ml of ethylacetate was added to the reaction mixture and stirred for about 15 minutes at 30 C. The layers were separated, and the aqueous layer was back extracted with 100 ml of ethylacetate. All the ethylacetate extracts were combined together and heated to reflux under stirring. 5 grams of activated charcoal was added, and the reaction mixture was stirred under reflux temperature for 30 minutes. The reaction mixture was filtered hot over a hyflo bed. 1.6 ml of water was added to the clear filtrate and heated to about 50 C. The reaction mass was stirred at 50 C. for 30 minutes and then concentrated under vacuum to keep about 100 ml of ethylacetate in the reaction mixture. 150 ml of isopropyl ether was added to the reaction mass and heated to reflux. 5 grams of activated carbon was added, and the reaction mixture was stirred under reflux for 30 minutes. The reaction mixture was filtered hot over a hyflo bed. The clear filtrate was cooled under stirring to about 30 C. and further chilled to about 5 C. The reaction mass was stirred at 5 C. to 10 C. for 1 hour. The resulting solid crystals were filtered and washed with 25 ml of chilled isopropyl ether. The product obtained was suck dried for 30 minutes and then dried at 65 C. under vacuum to get 40 grams of mirtazapine having HPLC purity of more than 99.8%.

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 61337-89-1, 2-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanol.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; US2011/201804; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde

Step 1 – Synthesis of[5-(5-chloro-lH-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-[6-(2,2,2- trifluoro-ethoxy)-pyridin-3-ylmethyl]-amine (P-0409):; [0254] To 5-(l -benzenesulfonyl-5-chloro-lH-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2- ylamine (599, 124.1 mg, 0.31 mmol, prepared as described in Example 29, Scheme 185) in ethanol (3.00 mL) and acetic acid (0.2 mL) were added 6-(2,2,2-trifluoro-ethoxy)-pyridine-3- carbaldehyde (603, 164.0 mg, 0.80 mmol) and silica supported cyanoborohydride (1.21 mmol/g, 0.700 g). The reaction was irradiated with microwave on 300 watts, 1000C for 150 minutes. To the reaction was added a solution of potassium hydroxide (9.0 M in water, 1.0 mL). The reaction was irradiated with microwave on 300 watts, 100 0C for 10 minutes. The reaction was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (P-0409, 10.6 mg, 7.6%). MS ESI) [M+H+]+ = 448.4.

With the rapid development of chemical substances, we look forward to future research findings about 159981-19-8.

Reference:
Patent; PLEXXIKON, INC.; WO2008/63888; (2008); A2;,
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.102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), molecular formula is C11H8N2O2S, molecular weight is 232.2584, as common compound, the synthetic route is as follows.HPLC of Formula: C11H8N2O2S

Steps b, c : N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide. A similar procedure to that described for the synthesis of N-(cis-(3-isothiocyanatocyclobutyl))-5-methoxy-[2,3′-bipyridine]-6′-carboxamide step c) and step d) was followed by using tert-butyl((cis)-3-(3-(4-methoxyphenyl)bicyclo[1.1.1]pentane1carboxamido) cyclobutyl) carbamate (58.0 mg, 0.15 mmol) to produce N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide (26.0 mg, 52%). 1H NMR (400 MHz, CDCl3): delta 7.14 (d, J=8.0 Hz, 2H); 6.67 (brs, 1H); 5.75-5.63 (brs, 1H); 4.25-4.13 (m, 1H); 3.90-3.81 (m, 1H); 3.80 (s, 3H); 2.95-2.70 (m, 2H); 2.25 (s, 6H); 2.24-2.15 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102368-13-8, 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), and friends who are interested can also refer to it.

Reference:
Patent; Northeastern University; Malamas, Michael S.; Makriyannis, Alexandros; Farah, Shrouq I.; Zvonok, Alexander M.; Alapafuja, Shakiru Olajire; (47 pag.)US2019/345132; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 931105-37-2, 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 931105-37-2, name is Methyl 5-bromo-2-fluoronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To an oven-dried 10 mL vial were added methyl 5-bromo-2-fluoronicotinate (1 g, 4.27 mmol), bis(pinacolato)diboron (217 mg, 0.854 mmol) and potassium acetate (1.258 g, 12.82 mmol). 1,4-Dioxane (20 mL) was introduced into the vial and nitrogen gas was blown through for 10 min. PdCl2(dppf) (0.156 g, 0.214 mmol) was added to the reaction mixture and degassing continued for 10 min. The mixture was heated to reflux at 80 C ON. The reaction mixture was filtered through a pad of Celite to remove the catalyst, and the filter cake was washed with EtOAc twice. The obtained organic solutions were concentrated. The crude residue was purified by flash column chromatography (ISCO, 80 g silica gel column, 20-50% EtOAc/hexanes) to yield methyl 2-fluoro-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1 g, 3.56 mmol, 83 %) as a white solid. MS ESI m/z 200.0 (M+H for the boronic acid)

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 931105-37-2, Methyl 5-bromo-2-fluoronicotinate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 71702-01-7, name is 5-Bromo-6-chloronicotinonitrile. A new synthetic method of this compound is introduced below., Computed Properties of C6H2BrClN2

Step 5; 3-Bromo-4- (3-bromo-5-cyano-pyridin-2-yloxy)-benzyl]- (3-methyl-butyl)-carbamic acid tert-butyl ester; Heat a mixture of the phenol obtained in step 4 (677 mg, 1.82 mmol), 5-Bromo-6-chloro- nicotinonitrile (395 mg, 1.82 mmol), K2CO3 (277 mg, 2.0 mmol) and DMF (22 mL) at 100C under N2 atmosphere overnight. Cool at room temperature. Pour into ice-water and extract with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography on silica gel (eluent : hexane/EtOAc 8/1) to afford the title compound (860 mg, 85%). H-NMR (CDCl3, 300 MHz): 8.30 (d, 1H, J= 2.0 Hz), 8.19 (d, 1H, J= 2.0 Hz), 7.53 (s, 1H), 7.29 (m, 1H), 7.18 (d, 1H, J= 8.3 Hz), 4.43 (m, 2H), 3.19 (m, 2H), 1.58-1. 42 (m, 12H), 0.90 (d, 6H, J= 6.5 Hz).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 71702-01-7, 5-Bromo-6-chloronicotinonitrile.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/90337; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5349-17-7, 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 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows.

Example 136: 4-(4-Pyridin-4-yl-thiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester A solution of 2-bromo-1-pyridin-4-yl-ethanone hydrobromide (35mg, 124mol) and 4- thiocarbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 18,34mg, 124Rmol) in methanol (2ml) was heated at 60C for 1. 5h. The reaction mixture was diluted with EtOAc (60ml), washed with saturated aqueous NaHCO3 (15ml) and brine (15ml) then dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (EtOAc) to afford the title compound: RT = 2.95min, mlz (ES+) = 376.1 [M+H] +.

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 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; PROSIDION LIMITED; WO2005/61489; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1235865-75-4, 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 1235865-75-4 as follows.

The mixture of (S)-6-(2- (2-cyclopropylphenyl) pyrrolidin-1-yl) -2-azaspiro [3.3] heptane (28.3 g, 0.1 mmol), methyl 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4-fluorobenzoate (31.57 g, 0.11 mmol), Na 2CO 3 (106 g, 1 mol) in DMF (500 mL) was heated to 105 C and stirred for overnight. After cooled to room temperature, the reaction mixture was diluted with EA (1000 mL), washed with brine (1000 mL 2), dried over Na 2SO 4 and concentrated in vacuum to afford a residue, which was purified by chromatography column on silica gel (eluent: EA/PE = 1/5 to 1/1) to give the product (11.2 g) as an off-white solid. MS (ESI, m/e) [M+1] + 548.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235865-75-4, its application will become more common.

Reference:
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53937-02-3, 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.53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, molecular formula is C12H11NO2, molecular weight is 201.22, as common compound, the synthetic route is as follows.

1-Bromobutane (3.75 g, 27.33 mmol) and potassium carbonate (10.3 g, 74.52 mmol) were added to a solution of 4-benzyloxy-7H-pyridin-2-one (5.0 g, 24.84 mmol) in acetonitrile (200 ml) and the mixture was heated at reflux for 16 hours. The reaction mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude residue was then triturated with diethylether to yield pure D4 (6.26 g, 98 %) as a white solid.

Statistics shows that 53937-02-3 is playing an increasingly important role. we look forward to future research findings about 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; WO2009/33704; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 164513-39-7 ,Some common heterocyclic compound, 164513-39-7, molecular formula is C7H8BrNO, 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.

General procedure: General procedure for the synthesis of example compounds in a library setupMethod AStep 1 : To a solution of the required building block (1 eq.) in toluene (10 mL) in a sealed tube, K2C03 (3 eq.), the corresponding bromo compound (1.2 eq) and /V./V-dimethylethylene diamine (0.5eq) were added. The RM was degassed by purging Ar for 30 min. Then, Cul (0.5 eq.) was added and Argon was purged for further 30 min. The tube was sealed with a Teflon screw cap and the RM was stirred at 100C for 2 to 6 d. The RM was cooled to rt and diluted with toluene (20 mL) and filtered over a plug of celite. The combined filtrate was concentrated under reduced pressure. The residue was purified by CC (silica gel) to afford the respective products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,164513-39-7, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem