Day: March 11, 2021

Electric Literature of 1072-97-5, 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.1072-97-5, name is 5-Bromopyridin-2-amine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.

A 1,2-dimethoxyethane solution (100 mL) of 2-amino-5-bromo-pyridine (5.19 g) and ethyl bromopyruvate (5.65 mL) was stirred for 2 hours at room temperature. The precipitated solid was filtered out, suspended in ethanol (180 mL) and refluxed for 2.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was neutralized with saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The extract was washed with saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate-hexane to obtain ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate (5.48 g) as colorless crystals. 1H-NMR (300MHz, CDCl3); delta 1.44 (3H, t, J=7.2Hz), 4.46 (2H, q, J=7.2Hz), 7.31 (1H, dd, J=1.8, 9.6Hz), 7.59 (1H, d, J=9.6Hz), 8.14 (1H, s), 8.29 (1H, d, J=1.8Hz)

Statistics shows that 1072-97-5 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyridin-2-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1849465; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6313-54-8, Adding some certain compound to certain chemical reactions, such as: 6313-54-8, name is 2-Chloroisonicotinic acid,molecular formula is C6H4ClNO2, 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 6313-54-8.

2-Chloroisonicotinic acid (200 mg, 1.26 mmol), N,N-diethylethylenediamine (0.2 mL, 30 1.39 mmol), HOBT (257 mg, 1.90 mmol) and EDCI (365 mg, 1.90 mmol) were dissolved in dry DMF (Aldrich anhydrous, 2 mL) under N2. Diisopropylethylamine (0.49 mL, 2.83 mmol) was added to the mixture and the reaction stirred o/n at RT. Following complete consumption of the acid by TLC the reaction was diluted with H2O (2OmL) and extracted with DCM (3 x 2OmL). The organics were combined, washed with water (4 x 20 mL), dried over MgSO4, filtered and evaporated to a crude oil, from which the title compound was purified by silica gel column chromatography using EtOAc-MeOH-NH3 (5-1 -trace) as the mobile phase as a clear oil (210 mg, 65 %). 1H NMR (CDCl3, 400 MHz) delta: 8.48 (d, J = 5.2 Hz, IH, Ar-H-6), 7.64 (s, IH, Ar-H-3), 7.49 (dd, J = 5.2, 1.6 Hz, IH, Ar-H-5), s 7.07 (bs, IH, NH), 3.40 (q, J = 5.6 Hz, 2H, CONH-CH2-CH2), 2.64 (t, J = 5.6 Hz, 2H, CONH-CH2-CH2), 2.58 (q, J = 6.8 Hz, 4H,N-(CH2-CH3)2), 1.03 (t, J = 6.8 Hz, 6H, N- (CH2-CH3)2). 13C NMR (CDCl3, 100 MHz) delta: 163.8 (CONH), 152.4 (Ar-CH-Cl), 150.3 (Ar-CH-6), 144.8 (Ar-CH-CONH), 122.1 (Ar-CH-3), 119.5 (Ar-CH-5), 50.5 (CONH- CH2-CH2), 46.7 (N-(CH2-CH3)2), 37.2 (CONH-CH2-CH2), 11.7 (N-(CH2-CH3)2). o LRMS ES(+) 258.1 (21 %), 256 (64 %, M+H+), 185 (32 %), 183 (100 %).

According to the analysis of related databases, 6313-54-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION; WO2009/129573; (2009); 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. 881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate, molecular formula is C9H9NO4, 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. HPLC of Formula: C9H9NO4

Step 1: Intermediate 32-b To a solution of dimethyl pyridine-2,5-dicarboxylate (13.0 g, 66.6 mmol) in a mixture of THF (110 mL) and ethanol (110 mL) was added calcium chloride (29.6 g, 266 mmol). After stirring at room temperature for 30 minutes the reaction was cooled to 0C and sodium borohydride (3.78 g, 100 mmol) was added portion wise. After the addition was completed the reaction was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride and dichloromethane were added, the organic layer was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried over MgS04, filtered and concentrated under reduced pressure to provide intermediate 32- b as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 881-86-7.

Reference:
Patent; PHARMASCIENCE, INC.; LAURENT, Alain; ROSE, Yannick; JAQUITH, James B.; WO2013/177668; (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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.Computed Properties of C5H5ClN2

N-iodosuccinimide (15.75 g, 70 mmol) was added to a solution of 2-chloropyridin-4-amine (9.00 g, 70 mmol) in N,N’-dimethylformamide (140 mL) and the mixture was stirred at 80 C for 6 hours. Further N-iodosuccinimide (7.80 g, 35 mmol) was added and the mixture was stirred at 60 C overnight. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium thiosulphate, water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (6:1 to 2:1 hexanes/ethyl acetate) to yield the title compound (6.80 g, 38%) as a beige solid. LRMS (m/z): 255 (M+1)+. 1H-NMR delta (CDCl3): 4.77 (brs, 2H), 6.63 (s, 1H), 8.34 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); 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

Electric Literature of 14254-57-0, 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 14254-57-0 as follows.

Compound 1 (455 mg, 0.64 mmol) was dissolved in 10 mL of dry dichloromethane,Additional triethylamine (130 mg, 1.28 mmol) was added. Compound 2 (272 mg, 1.92 mmol) was added portionwise to the reaction under ice-water bath conditions. The reaction liquid nitrogen protection, 0 C for half an hour, then at room temperature for 5 hours, TLC detection reaction was complete. To the reaction mixture was added 150 mL of methylene chloride, and the organic phase was washed with saturated brine (150 mL ¡Á 3) and dried over anhydrous sodium sulfate. Suction filtration and distillation under reduced pressure to give the crude product, which was purified by column chromatography with methylene chloride / methanol = 20/1 to obtain 425 mg of the pure product of Intermediate 3 as a yellow solid in a yield of 81.4%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14254-57-0, its application will become more common.

Reference:
Patent; Shandong University; Zhao Baoxiang; Miao Junying; Zhang Xiaofan; Zhao Xuan; (10 pag.)CN106632363; (2017); A;,
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. 143468-13-7, name is 6-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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: 6-Bromo-1H-pyrrolo[2,3-b]pyridine

General procedure: To a degassed 3.5:1 mixture of dimethoxyethane and water (2mL), compound 5 (0.5mmol), the appropriate boronic acid (1mmol), PdCl2(dppf)CH2Cl2 (0.025mmol) and sodium bicarbonate (1.5mmol) were added under nitrogen. The mixture was heated for 1-4h. The layers were separated and the organic phase was evaporated. Purification by flash chromatography gave the desired compounds. Following this procedure compounds 1m-n, 6b-e, 6g-h, 6j, 6l-m, 11, 15 were prepared.

With the rapid development of chemical substances, we look forward to future research findings about 143468-13-7.

Reference:
Article; Cincinelli, Raffaella; Musso, Loana; Merlini, Lucio; Giannini, Giuseppe; Vesci, Loredana; Milazzo, Ferdinando M.; Carenini, Nives; Perego, Paola; Penco, Sergio; Artali, Roberto; Zunino, Franco; Pisano, Claudio; Dallavalle, Sabrina; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1089 – 1103;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7418-65-7 , The common heterocyclic compound, 7418-65-7, name is 4-Aminonicotinic acid, molecular formula is C6H6N2O2, 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.

2-Methyl-4H-pyrido[4,3-d][1,3]oxazin-4-one (17): The suspension of 16 (1.0 g, 7.3 mmol) in 6 mL of acetic anhydride was stirred under reflux for 2 h. The resulting orange solution was cooled to RT. The reaction mixture was concentrated in vacuo and the product was recrystallized from EtOAc to afford 0.65 g of compound 17 (56% yield).

The synthetic route of 7418-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; Chong, Jayhong A.; Fanger, Christopher; Larsen, Glenn R.; Moran, Magdalene M.; Ng, Howard; Ripka, Amy; Underwood, Dennis John; Weigele, Manfred; Zhen, Xiaoguang; (83 pag.)US9486455; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17368-12-6, 2-Chloro-4-hydroxypyridine, 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, Computed Properties of C5H4ClNO, blongs to pyridine-derivatives compound. Computed Properties of C5H4ClNO

Example A2: 2-Chloro-4-hydroxypyridine (0.319 g, 2.460 mmol) was dissolved in DMF ( 1 0 mL) under argon and cooled to – 15 C. Sodium hydride (60%> in mineral oil) (0.148 g, 3.69 mmol) was added slowly and the mixture was stirred for 15 minutes. 5-Chloro-2,4- difluoronitrobenzene (0.5 g, 2.58 mmol) was then added all at once as a solution in DMF (2 mL). The reaction mixture stirred at – 15 C for 1 hour and then additional 5-chloro-2,4- difluoronitrobenzene (0.075g) was added. The mixture stirred at – 15 C for an additional 1 5 hours and was then warmed to room temperature and diluted with ethyl acetate ( 100 mL) and washed with 10% aqueous lithium chloride (3 x 75 mL) and brine (75 mL). The organic layer was dried over magnesium sulfate and evaporated to yield an orange oil, which was then purified by silica gel chromatography (0 to 30% ethyl acetate/hexane) to give 2-chloro-4-(2-chloro-5- fluoro-4-nitrophenoxy)pyridine (0.64g, 86%yield) as a light yellow oil. 1H NMR (400MHz, DMSO-i/6): delta 8.57 (dd, 1 H), 8.36 (dd, 1 H), 7.87 (dd, 1 H), 7.32 (dd, 1 H), 7.19 (m, 1 H); MS (ESI) m/z: 303.0 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17368-12-6, 2-Chloro-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2011/137342; (2011); 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