Tag: M.W:200-300

Electric Literature of 55304-75-1, 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 55304-75-1 as follows.

To a suspension of tert-butyl-1-piperazine carboxylate (27.0 g, 145 mmol) and K2CO3 (40.0 g, 290 mmol) in DMSO (200 ML) were 2,6-dichloro-3-trifluoromethylpyridine (29.1 g, 135 mmol) and toluene (50 ML) added.The thick slurry was stirred at 80 C. for two hours, followed by addition of toluene (0.5 L) and water (1 L).The phases were separated and the organic phase was washed twice with water.The solvent from the dried (MgSO4) organic phase was evaporated at reduced pressure.The solid residue was recrystallized from EtOAc/heptane to give white crystals (37 g).The filtrate from the recrystallization was concentrated and the residue chromatographed on a column of silica with hexane/EtOAc (90:10) to give further 6.0 g of product (total yield 85%).Purity 99% (HPLC); mp 125 C. Anal. (C15H19ClF3N3O2) C, H, N.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55304-75-1, its application will become more common.

Reference:
Patent; Nilsson, Bjorn M.; Ringberg, Erik; US2003/232814; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1123194-98-8 , The common heterocyclic compound, 1123194-98-8, name is 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, molecular formula is C10H10BrN3O, 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 stirred solution6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl) pyridine (20 g, 74 mmol) in DMF (240 mL) at room temperature under an argon atmosphere were added Pd(dppf)2C12 (500 mg, 0.9 mmol), Pd2(dba)3 (682 mg, 0.7 mmol) and zinc cyanide (5.3 g, 45 mmol). The reaction mixture was stirred at 140 C for 2 h. After consumption of starting material (monitored by TLC), the reaction mixture was diluted with 25% NH4OH solution (240 mL) to afford the solid. The solid was collected by filtration and dried in vacuo to afford 6-methoxy-5-(4- methyl-1H-imidazol-1-yl) picolinonitrile (14 g, 88%) as a pale yellow solid.[0872] ?H NMR (CDC13: 400 MHz): 7.89 (s, 1H), 7.63 (d, 1H), 7.43 (d, 1H), 7.01 (s, 1H), 4.09 (s, 3H), 2.30 (s, 3H); LCMS: 98.7%; 214.9 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 pm); RT 1.19 mm; mobile phase: 0.025% Aq TFA+5% ACN:ACN+5% 0.025% Aq TFA; T/B%: 0.0 1/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: EtOAc (R1 0.3).

The synthetic route of 1123194-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); 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.916325-85-4, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H4BrN3O2, molecular weight is 242.03, as common compound, the synthetic route is as follows.name: 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XXXIV) (1.6 Kg, 6.6 mol) in anhydrous MeOH (32 L) was added H2SO4 (160 mL). The reaction was slowly heated to 70oC and stirred for 20 hours. The solution was concentrated under vacuum to a volume of 1.6 L. The residue was partitioned between DCM (120 L) and aqueous 10% NaHCO3 (32 L). The organic phase was separated and washed with aqueous 25% NaCl (32 L), dried over Na2SO4 and concentrated to a volume of 4.8 L. The product was crystallized by charging the solution with 3 x n-heptane (8 L) while concentrating the volume to 4.8 L after each addition of n- heptane. The solid was filtered and dried under vacuum at 50oC to produce methyl 5-bromo-1H- pyrazolo[3,4-b]pyridine-3-carboxylate (XXXV) (1.53 Kg, 6.0 mol, 80.6% purity, 90.4% assay yield).1H NMR (DMSO-d6, 400 MHz) d ppm 3.95 (s, 3H), 8.62 (d, J=2Hz, 1H), 8.73 (d, J=2.4Hz, 1H), 14.78 (brs, 1H); ESIMS found C8H6BrN3O2 m/z 256.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,916325-85-4, 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; MITTAPALLI, Gopi Kumar; CHIRUTA, Chandramouli; HOFILENA, Brian Joseph; (128 pag.)WO2019/241540; (2019); A1;,
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. 1659-31-0, name is Dipyridin-2-yl carbonate, molecular formula is C11H8N2O3, 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. Recommanded Product: 1659-31-0

Under nitrogen atmosphere, to a stirred mixture of (4-cyclohexylphenyl)-methanol (0.3 g, 1.58 mmol) in dry CH2Cl2 (2 mL), DMAP (0.019 g, 0.16 mmol) and di-2-pyridyl-carbonate (0.411 g, 1.90 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2Cl2 and washed first with a saturated NH4Cl solution (3.0 mL) and subsequently with a saturated NaHCO3 solution (3¡Á3 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford a colorless oil (0.464 g, 95%), as a mixture (ratio 1.8:1) of (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and (4-cyclohexylphenyl)-methyl-2-oxopyridine-1-carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z: 350 [M-K]+.

With the rapid development of chemical substances, we look forward to future research findings about 1659-31-0.

Reference:
Patent; The Regents of the University of California; Fondazione Istituto Italiano Di Technologia; Universita Degli Studi Di Parma; Universita Degli Studi Di Urbino ?Carlo Bo?; Piomelli, Daniele; Bandiera, Tiziano; Mor, Marco; Tarzia, Giorgio; Bertozzi, Fabio; Ponzano, Stefano; (102 pag.)US9353075; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 944401-56-3, 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 944401-56-3, name is 5-Bromo-4-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyridin- 2-amine:To a dry 25 ml flask was added 5-bromo-4-(trifluoromethyl)pyridin-2-amine (300 mg, 1.24 mmol, 1.0 eq.), potassium acetate (366 mg, 3.73 mmol, 3.0 eq.), bis(pinacolato)diboran (348 mg, 1.37 mmol, 1.1 eq.) and dioxane (8 ml). Argon was bubbled through the solution for 15 minutes, at which time 1 ,1- bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (50.8 mg, 60 mumol, 0.05 eq.) was added. The reaction was refluxed in a 115 0C oil bath for 8 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. Ethyl acetate was added and the resulting slurry was sonicated and filtered. Additional ethyl acetate was used to wash the solid. The combined organic extracts were concentrated and the crude material was partially purified by silica gel chromatography (hexane/ethyl acetate 6:4). Upon removal of solvent, hexane was added, decantation was done and resulting colorless solid was dried on a high vacuum for three days. Analytical data:1H NMR (400 MHz, CDCI3): delta 8.49 (S1 1H), 6.71 (s, 1H), 4.86 (s, 2H), 1.33 (s, 12H),1.27 (s, 2H), 1.24 (s, 2H).19F (400 MHz, CDCI3): delta -64.24.ESI-MS (70 eV, m/z): calcd. for Ci2H16BF3N2O2 [M+H] +: 289.13, found 289.10.

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 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; UNIVERSITY OF BASEL; CMILJANOVIC, Vladimir; CMILJANOVIC, Natasa; GIESE, Bernd; WYMANN, Matthias; WO2010/52569; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59237-53-5, 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.59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, molecular weight is 216.58, as common compound, the synthetic route is as follows.

To a solution of methyl 6-chloro-5-nitronicotinate (700 mg, 3.23 mmol) in CH2CI2 (20 mL) were added (2-methyloxazol-4-yl)methanamine (362 mg, 3.23 mmol) and N,N- diisopropylethylamine (0.734 mL, 4.20 mmol), and the reaction mixture was stirred at room temperature for 20 hours. The mixture was concentrated, and the resulting residue was washed with water and dried under vacuum to give the desired product (920 mg) as a pale yellow solid. LC-MS (ES) m/z = 293 [M+H]+. NMR (400 MHz, CD3OD): 5 2.45 (s, 3H), 3.93 (s, 3H), 4.79 (d, J = 1 .0 Hz, 2H), 7.74 (t, J = 1 .0 Hz, 1 H), 8.93 – 8.96 (m, 1 H), 8.96 – 8.99 (m, 1 H).

Statistics shows that 59237-53-5 is playing an increasingly important role. we look forward to future research findings about Methyl 6-chloro-5-nitronicotinate.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13959-02-9 ,Some common heterocyclic compound, 13959-02-9, molecular formula is C6H4BrNO2, 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 ;To a mixture of 3-bromoisonicotinic acid (2.5 g, 12.37 mmol, 1 eq.) and TEA (3.44 mL, 24.75 mmol, 2.0 eq.) in THF (100 mL) was added methyl chloroformate (1.2 mL, 14.85 mmol, 1.2 eq.) at 0 C. The mixture was stirred at 0 C. for 10 min and filtered. To this filtrate was added a suspension of NaBH4 (0.95 g, 24.75 mmol, 2 eq.) in water (1.0 mL) at 0 C. The mixture was stirred at 0 C. for 1 h, quenched with NH4Cl(aq) solution, extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-bromopyridin-4-yl)methanol (1.2 g, 52%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.48 (s, 1H), 8.37 (d, J=4.9 Hz, 1H), 7.37 (d, J=4.9 Hz, 1H), 4.61 (d, J=5.5 Hz, 2H), 2.3 (t, J=5.5 Hz, 1H). LRMS (M+H+) m/z 188.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13959-02-9, its application will become more common.

Reference:
Patent; Global Blood Therapeutics, Inc.; The Regents of the University of Califorina; Cytokinetics, Inc.; Metcalf, Brian; Chuang, Chihyuan; Warrington, Jeffrey; Paulvannan, Kumar; Jacobson, Matthew P.; Hua, Lan; Morgan, Bradley; US2015/344483; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 70201-42-2, 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. 70201-42-2, name is 3,5-Dibromoisonicotinaldehyde, molecular formula is C6H3Br2NO, 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 109a 3-Bromo-5-(6-tert-butyl-8-fluoro-1-oxo-1,2-dihydrophthalazin-2-yl)pyridine-4-carbaldehyde 109a A sealed tube equipped with a magnetic stirrer was charged with 6-tert-butyl-8-fluoro-1,2-dihydrophthalazin-1-one 101h (220 mg, 1.0 mmol), 3,5-dibromopyridine-4-carbaldehyde (530 mg, 2.0 mmol), CuI (190 mg, 1.0 mmol), 4,7-dimethoxy-1,10-phenanthroline (244 mg, 1.0 mmol), Cs2CO3 (652 mg, 2.0 mmol) and dioxane (8 mL). After three cycles of vacuum/argon flush, the mixture was heated at 110 C. for 5 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3, V/V) to afford 109a (118 mg, 29.3%) as a solid. LCMS: [M+H]+ 406

According to the analysis of related databases, 70201-42-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); 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.845306-08-3, name is tert-Butyl 5-bromopicolinate, molecular formula is C10H12BrNO2, molecular weight is 258.11, as common compound, the synthetic route is as follows.name: tert-Butyl 5-bromopicolinate

24. Subjection of ethyl bromo(difluoro)acetate and fe/f-butyl 5-bromopyridine-2- carboxylate to copper powder in dimethyl sulfoxide provided fe/f-butyl 5-(2-ethoxy-1 , 1 – difluoro-2-oxoethyl)pyridine-2-carboxylate. Reduction of the ethyl ester to the primary alcohol was carried out with sodium borohydride in ethanol; subsequent methyl ether formation with iodomethane and silver(l) oxide afforded fe/f-butyl 5-(1 , 1 -difluoro-2- methoxyethyl)pyridine-2-carboxylate. Treatment with trifluoroacetic acid then generated the requisite 5-(1 , 1 -difluoro-2-methoxyethyl)pyridine-2-carboxylic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,845306-08-3, tert-Butyl 5-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; BECK, Elizabeth Mary; BUTLER, Christopher Ryan; ZHANG, Lei; O’NEILL, Brian Thomas; BARREIRO, Gabriela; LACHAPELLE, Erik Alphie; ROGERS, Bruce Nelsen; WO2015/155626; (2015); A1;,
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. 197376-41-3, name is Ethyl 2-(3-Bromo-2-pyridyl)acetate, molecular formula is C9H10BrNO2, 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. Recommanded Product: 197376-41-3

Example 583-[4-Chloro-3-[[(tricyclo[3.3.1.13’7]dec-l-ylmethyl)amino]carbonyl]phenyl]-2-pyridineacetic acid, monosodium saltoCl[4-Chloro-3-[[(tricyclo[3.3.1.13’7]dec-l-ylmetliyl)amino]carbonyl]phenyl]-boronic acid(Example 2(a)) (142 mg), 3-bromo-2-pyridineacetic acid ethyl ester (Prepared according tothe method of Synthesis, 1997, 949-952) (100 mg), sodium carbonate (130 mg),te^rafaXtriphenylphosphme)paUadium(O) (10 mg), tetrahydrofuran (2 mL) and water (1mL) were heated in a microwave at 120 C for 30 minutes. 48% sodium hydroxide solution(200 uL) was added to the reaction which was stirred for 12 hours before being filtered.The solid was washed with water (3 mL) and then acetonitrile (3 mL) before being dried ina vacuum oven to afford the title compound as a solid (55 mg).MS: APCI(-ve) 437m.p. 186-1 87C dec.JH NMR (300 MHz, d6-DMSO) 5 8.61 (1H, t), 8.44 (1H, d), 7.72 (1H, dd), 7.61 – 7.55(2H, m), 7.49 (1H, d), 7.26 – 7.19 (1H, m), 3.29 (2H, s), 2.94 (2H, d), 1.93 (3H, s), 1.701.50(12H,m).

With the rapid development of chemical substances, we look forward to future research findings about 197376-41-3.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem