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.178876-83-0, name is Methyl 6-amino-3-bromopicolinate, molecular formula is C7H7BrN2O2, molecular weight is 231.0467, as common compound, the synthetic route is as follows.Recommanded Product: 178876-83-0

To a 25 mL round bottom flask, were added methyl 6-amino-3-bromopicolinate (1 g, 0.0043 mol), 3-fluorophenylboronic acid (0.72 g, 0.0052 mol), potassium carbonate (1.52 g, 0.011 mol), 1,4-dioxane (20 mL) and water (4 mL). The reaction mixture was degassed with nitrogen for 5 min. To the same flask, bis(triphenylphosphine)palladium(II) dichloride (0.14 g, 0.00022 mol) was added. The reaction mixture was again degassed with nitrogen for 5 min. The reaction mixture was stirred at 90 C for 2 h. The volatiles were evaporated under reduced pressure to get the residue. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get the crude product. The crude product was purified by flash column chromatography using 20 – 40 % ethyl acetate in hexane to obtain the title compound [0.6 g, 57 %]. FontWeight=”Bold” FontSize=”10″ H NMR (CDC13, 400 MHz): delta 7.68-7.63 (m, 1H), 7.48 (d, = 8.8 Hz, 1H), 7.36-7.31 (m, 1H), 7.05-6.97 (m, 2H), 6.67 (d, = Hz, 1H), 4.79 (brs, 2H), 3.72 (s, 3H); LC-MS: 247.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178876-83-0, Methyl 6-amino-3-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BEJUGAM, Mallesham; HOSAHALLI, Subramanya; MAHALINGAM, Natarajan; WO2014/125426; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 936342-91-5, 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. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, molecular formula is C6H6BrCl2N, 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.

A mixture of 5-bromo-2-methylpyridine (500mg, 2.06mmol) and 1-methanesulfonyl-piperazine (440mg, 2.68mmol) was dissolved in N, N- dimethylformamide (10ml) was then added carbonate potassium (996mg, 7.21mmol), the reaction was stirred for 12 hours at room temperature, 100ml of water was added to the reaction mixture was cooled, (100ml * 3) and extracted with ethyl acetate, then with saturated sodium chloride solution (100ml * 2) and washed to give the organic phase was dried over anhydrous magnesium sulfate filtered, and concentrated under reduced pressure to give 1- (5-bromo – 2-methyl-pyridin) yl-4-methanesulfonyl – piperazine (520mg, white solid), yield: 75.6percent.

According to the analysis of related databases, 936342-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI CDYMAX PHARMACEUTICALS CO., LTD; An, Xiaoxia; Bie, Pingyan; Liu, Jun; Yang, Wuli; (42 pag.)CN103360407; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55404-31-4 , The common heterocyclic compound, 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, 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 3: In a sealed tube, NaOMe (25% in MeOH, 3.1 mL, 13 mmol) was added to a solution of compound 94 (1.8 g, 8.7 mmol) in MeOH (17 mL). The reaction was heated at 75 C for 3 days. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with saturated NH4CI and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography over silica gel, which was eluted with heptanes/EtOAc (0-15%) to afford compound 95 as a clear oil (991 mg, 56% yield). 1H NMR (400 MHz, DMSO-c/6) delta 8.00 (d, J = 5.0 Hz, 1 H), 6.98 (d, J = 4.8 Hz, 1 H), 3.90 (s, 3 H), 2.35 (s, 3 H).

The synthetic route of 55404-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
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Reference of 955372-86-8, Adding some certain compound to certain chemical reactions, such as: 955372-86-8, name is 3-Bromo-5-fluoroisonicotinic 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 955372-86-8.

A mixture of 3-bromo-5-fluoroisonicotinic acid (5a, 1 .87 g, 8.5 mmol) and HATU (4.85 g, 12.75 mmol) in DMF (30 ml) was added DIEA (4.5 ml), the mixture was stirred at r.t for 20 minutes, then isonicotinimidamide (1 .236 g, 10.2 mmol) was added. Stirring was continued for another 15 hours at r.t. The reaction mixture was concentrated under reduced pressure. The light brown syrup crude mixture was then dissolved in DCM and purified by silica gel chromatography (eluted with 0-10% MeOH/solvent A, solvent A is mixture of 4 liter DCM and 8 ml of 7N ammonia solution in MeOH), fractions 66-80 were pooled and concentrated to afford the desired product 3-bromo-5-fluoro-N-(imino(pyridin-4- yl)methyl)isonicotinamide 5b (566 mg, 20.6%). 1 H NMR (500 MHz, DMSO-d6) delta 10.27 (s, 1 H), 10.09 (s, 1 H), 8.79 – 8.73 (m, 2H), 8.71 (s, 2H), 7.95 – 7.89 (m, 2H). LCMS (m/z [M+H]+): 323.0.

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. 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; BERENSHTEYN, Frada; HAO, Xueshi; HOFFMAN, Timothy; JIN, Qihui; LACOSTE, Arnaud; LEE, Cameron; LIU, Jun; LIU, Yahu; MAIBAUM, Juergen Klaus; MO, Tingting; PAN, Jianfeng; QU, Xin; TCHORZ, Jan; XIE, Yun Feng; YAN, Shanshan; ZOU, Yefen; (564 pag.)WO2018/198077; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 623585-74-0, Adding some certain compound to certain chemical reactions, such as: 623585-74-0, name is Methyl 2,5-dichloroisonicotinate,molecular formula is C7H5Cl2NO2, 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 623585-74-0.

To a solution of methyl 2,5-dichloroisonicotinate (2.25 g) in THF (50 mL) was added sodium borohydride (0.828 g), ethanol (20 mL) was added dropwise, and the mixture was stirred at 50C for 4 hr. To the reaction mixture was added 1 M aqueous hydrochloric acid solution. The solvent was evaporated under reduced pressure, and the obtained residue was diluted with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.90 g). MS (ESI+) : [M+H]+177.8.

According to the analysis of related databases, 623585-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); 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.1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, molecular weight is 206.2874, as common compound, the synthetic route is as follows.SDS of cas: 1018505-59-3

4-(2-Chloro-3-fluoro-pyrazinylamino)-2-pyrimidinecarboxylic acid (1.35 g, 1.2 eq),5-(4-Ethyl-piperazin-1-yl)-piperidin-2-amino (0.81 g, 1 eq) and triethylamine (500 muL)In DMF (15 mL) followed by HBTU (1.51 g, 1.5 eq).The mixture was stirred at room temperature for 16 hours.Then EtOAc (50 mL) and saturated NaHCO3 (15 mL)The layers were separated and the aqueous layer was extracted with EtOAc EtOAcThe combined organic layers were dried (MgSO4), filtered and evaporated.The residue was purified by column chromatography.1.42 g of the target compound 2 was obtained as a white solid(yield: 62%),Its nuclear magnetic resonance spectrum data is as follows:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Hu Xiande; Zhou Liming; Sui Guilan; (22 pag.)CN109568256; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62150-46-3 ,Some common heterocyclic compound, 62150-46-3, molecular formula is C6H5BrN2O, 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.

(ii) (S)-tert- uty l-(2-(4-(2-carbamoylpyridin-4-yl)phcyanoethylcarbamoyl)cyclohexylcarbamateA solution of (S)-tert-butyl l-(l-cyano-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (Example 23 step (i),569 mg), potassium acetate (225 mg) and 4-bromopicolinamide (230 mg) in mixture of acetonitrile (15 mL) and water (5 mL), was stirred under an atmosphere of nitrogen. 1,1¾z5(di-fert-butylphosphino)ferrocene palladium dichloride (22 mg) was added and the mixture heated at 90 C for 4h. The reaction mixture was concentrated to dryness and the residue purified on silica gel using ethyl acetate as eluant. Pure fractions were evaporated to dryness to afford the sub-titled compound (90 mg). m/e (APCI+) 490 [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. 62150-46-3, 4-Bromopicolinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (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. 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 3-Bromo-2-methoxy-5-nitropyridine

Step 1: tert-Butyl (1-(4-((2-methoxy-5-nitropyridin-3-yl)ethynyl)phenyl)cyclobutyl) carbamate: 3-Bromo-2-methoxy-5-nitropyridine (161 mg, 0.691 mmol) was stirred in 1 : 1 , Et3N/1 ,4-dioxane (1.5 mL) at RT and the reaction mixture degassed under an atmosphere of N2. The temperature was reduced to 0 C and Pd(‘Bu3P)2 (14.1 mg, 0.0276 mmol) was added. After 10 minutes, Cu(l)l (1.3 mg, 0.0092 mmol), followed by dropwise addition of tert-butyl (1-(4-ethynylphenyl)cyclobutyl)carbamate (125 mg, 0.461 mmol) in Et3N (0.75 mL). After 4 hours, the solvents were removed in vacuo, coevaporating to remove residual Et3N. The residue was dissolved in DCM, filtered through Celite, washing with DCM. The solvents were removed in vacuo and the remaining residue was purified by flash chromatography (Si02, 0?25%, EtOAc in n- hexane) to give the title compound (127 mg, 65%) as a pale yellow solid. 1H NMR (500 MHz, CDCI3): delta 9.00 (d, 1 H), 8.50 (d, 1 H), 7.55 (d, 2H), 7.44 (d, 2H), 5.13 (s, 1 H), 4.15 (s, 3H), 2.62-2.43 (m, 4H), 2.18-2.08 (m, 1 H), 1.94-1.83 (m, 1 H). 1.49-1.05 (m, 9H).

The synthetic route of 15862-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 902837-39-2, 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.902837-39-2, name is 3-Bromo-5-iodopyridin-4-amine, molecular formula is C5H4BrIN2, molecular weight is 298.91, as common compound, the synthetic route is as follows.

8-Bromo-4-methyl-1,6-naphthyridin-2(1H)-one To a solution of 3-Bromo-5-iodopyridin-4-amine (1.5 g, 5.02 mmol) in DMF (12 mL) was added methyl crotonate (1.064 mL, 10.04 mmol), triethylamine (0.974 mL, 7.03 mmol), tri-o-tolylphosphine (0.12 g, 0.401 mmol) and palladium(II)acetate (0.045 g, 0.201 mmol) under nitrogen and the mixture was stirred at 120 C. for 48 h. The DMF was evaporated (V10 biotage system) and the resulting residue was purified by chromatography on silica gel (biotage, CH2Cl2/MeOH, 100:0 to 92:8) to give the product (0.82 g, 69%) as a red solid. This solid was further purified by recrystallization from hot EtOAc to give the pure product (503 mg, 42%) as a beige solid.

Statistics shows that 902837-39-2 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-iodopyridin-4-amine.

Reference:
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886365-47-5, 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 886365-47-5, name is 1-(5-Bromo-2-chloropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-(5-bromo-2-chloropyridin-3- yl)ethanone (980 mg, 3.97 mmol) and N,N-dimethylformamide dimethyl acetal (4.0 mL, 30 mmol) was stirred at 90C for 90 minutes in an oil bath. The mixture was cooled to room temperature, and concentrated under reduce pressure. The residue was diluted by addition of ethanol (13 mL) and water (6.5 mL), acetic acid (1.6 mL, 28 mmol) and methyl (2S)-2-hydrazinylpropanoate hydrochloride (0.859 g, 5.56 mmol) obtained in Example (16a) was added thereto at room temperature, and the mixture was stirred at 90C for 4 hours in an oil bath. The mixture was cooled to room temperature, and neutralized by addition of a 2.0 mol/L aqueous solution of sodium hydroxide, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of (2S)-2-[5-(5-bromo-2- chloropyridin-3-yl) -1H-pyrazol-1-yl]propanoic acid (1.39 g) as a mixture containing a positional isomer. To a solution of the crude product of (2S)-2-[5-(5-bromo-2- chloropyridin-3-yl) -1H-pyrazol-1-yl]propanoic acid (1.31 g) obtained in the above step in tetrahydrofuran (10 mL), a 0.92 mol/L solution of boran-tetrahydrofuran complex in tetrahydrofuran (6.5 mL, 6.0 mmol) was added under ice cooling, the mixture was stirred at the same temperature as above for 10 minutes and subsequently stirred at room temperature for 20 hours. The mixture was cooled in an ice water bath, a 1.0 mol/L aqueous solution of sodium hydroxide was added thereto, followed by extraction with a mixed solvent of ethyl acetate/nhexane = 4/1. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain a crude product of (2S)-2-[5-(5-bromo-2- chloropyridin-3-yl) -1H-pyrazol-1-yl]propan-1-ol (760 mg) as a mixture containing a positional isomer. To a solution of the crude product of (2S)-2-[5-(5-bromo-2- chloropyridin-3-yl) -1H-pyrazol-1-yl]propan-1-ol (760 mg) as a mixture containing positional isomers obtained in the above step in N,N-dimethylformamide (50 mL) was added potassium carbonate (829 mg, 6.00 mmol) at room temperature, and the mixture was stirred at 120C for 2 hours in an oil bath. The reaction mixture was cooled, and diluted by addition of a saturated aqueous solution of ammonium chloride, followed by extraction with a mixed solvent of ethyl acetate/n-hexane = 4/1. The organic layer was washed with a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, the residue was purified in an automatic chromatography apparatus (Yamazen Co. Ltd., High-flashTM column Amino, n-hexane/ethyl acetate = 96/4- 66/34) to obtain the title compound (597 mg, yield for 3 steps: 54%)?H NNR spectrum (CDC13, 400MHz) oe: 8.26 (1H, d, J =2.4 Hz), 8.19 (1H, d, J= 2.4 Hz), 7.55 (1H, d, J=1.8 Hz), 6.66 (1H, d, J = 1.8 Hz), 4.95-4.89 (1H, m),4.59 (1H, dd, J = 13.1, 4.6 Hz), 4.44-4.43 (1H, m), 1.64 (3H, d, J= 7.3 Hz).

According to the analysis of related databases, 886365-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; MIYAZAKI, Shojiro; INUI, Masaharu; KUROSAKI, Yasunobu; YAMAMOTO, Yuko; IZUMI, Masanori; SOMA, Kaori; PINKERTON, Anthony; KISHIDA, Masamichi; (309 pag.)WO2018/119444; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem