Category: pyridine-derivatives

Application of 717843-56-6, 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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine. A new synthetic method of this compound is introduced below.

Example 172 (7bR,11aS)-N-(2-Methoxy-5-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from Example 56, Part B (968 mg, 2.81 mmol), 3-bromo-2-methoxy-5-methylpyridine (515 mg, 2.55 mmol), and NaOt-Bu (404 mg, 4.20 mmol) in anhydrous toluene (40 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon at 85 C. for 30 min then cooled to 50 C. Tris(dibenzylideneacetone)dipalladium(0) (62 mg, 67 mumol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (84.0 mg, 135 mumol) were added; the reaction was sealed and heated at 85 C. for 16 h. The reaction was cooled to room temperature, diluted with EtOAc, filtered through a bilayer pad of diatomaceous earth and silica gel, and concentrated. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-methoxy-5-methyl-3-pyridinyl)-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate (1.16 g, 89%). A solution of the intermediate in CH2Cl2 (20 mL) at -10 C. was treated with TFA (6 mL) and stirred for 1 h. Upon concentration in vacuo, the residue was partitioned between a 1:1 solution of CH2Cl2/satd NaHCO3 (100 mL). The aqueous phase was extracted with CH2Cl2 (4*75 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography [silica gel, 5-50% (80:18:2 CHCl3/MeOH/concd NH4OH)/CH2Cl2] and trituration with CH2Cl2/Et2O/hexanes provided the title compound of Example 172 (590 mg, 65%) as a tan solid: mp 122-124 C.; 1H NMR (300 MHz, CDCl3) delta 7.40 (s, 1H), 6.99 (s, 1H), 6.88 (s, 1H), 6.77 (s, 1H), 5.84 (br s, 1H), 4.75 (d, J=14.1 Hz, 1H), 4.58 (d, J=14.1 Hz, 1H), 4.34-4.16 (m, 1H), 4.01 (s, 3H), 3.89-3.69 (m, 1H), 3.58-3.39 (m, 1H), 3.38-3.13 (m, 2H), 3.11-2.99 (m, 1H), 2.98-2.85 (m, 2H), 2.81-2.68 (m, 1H), 2.61-2.42 (m, 1H), 2.19 (s, 3H), 2.01-1.77 (m, 3H); ESI MS m/z 367 [C21H26N4O2+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717843-56-6, 3-Bromo-2-methoxy-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Robichaud, Albert J.; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2004/186094; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 851484-95-2, Adding some certain compound to certain chemical reactions, such as: 851484-95-2, name is 2-Chloro-5-fluoronicotinaldehyde,molecular formula is C6H3ClFNO, 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 851484-95-2.

Example 37: Synthesis of 3-Fluoro-l,7,llb-triaza-benzo[c]fluorene-6-carboxylic acid ethyl es [0321] To a solution of compound SMI (0.8 g, 5 mmol) and compound SM2 (1.02 g, 5 mmol) in ethanol (50 mL) was added piperidine (1.28 g, 15 mmol) and the mixture was stirred at room temperature for 20 min. The reaction mixture was heated to reflux for 16h. After cooling, the mixture was filtered and washed with ethanol, dried to get compound 7A as yellow solid (0.82 g, 79 yield). LCMS: m/z 309.9 (M+H)+.

According to the analysis of related databases, 851484-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HADDACH, Mustapha; WO2015/172123; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1187830-47-2, 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine hydrochloride, 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, Formula: C6H10ClN3, blongs to pyridine-derivatives compound. Formula: C6H10ClN3

To a mixture of 4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine (500 mg, 3.13 mmol, HCl, CAS1187830-47-2) and (Boc)2O (752 mg, 3.45 mmol) in MeOH (15 mL) was added aq.K2CO3 (3 M, 2.09 mL). The reaction mixture was stirred at 20 C. for 15 hours. On completion, the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (SiO2) to give the title compound (500 mg, 71% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.05 (s, 1H), 7.55 (s, 1H), 3.66-3.55 (m, 2H), 2.65 (t, J=6.4 Hz, 2H), 1.94-1.82 (m, 2H), 1.51 (s, 9H).

The synthetic route of 1187830-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 86521-05-3, 2-((Trimethylsilyl)ethynyl)pyridine, 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, COA of Formula: C10H13NSi, blongs to pyridine-derivatives compound. COA of Formula: C10H13NSi

2-((Trimethylsilyl)ethynyl)pyridine (175mg, 1.0 mmol) was dissolved in MeOH/Dichloromethane (2mL/lmL). The solution was cooled to 0 C and KOH (112mg, 2.0 mmol) was added. The reaction mixture stirred for 0.5 h, and then quenched with H2O, extracted with Dichloromethane (2×3 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 2-ethynylpyridine (80 mg, 80% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86521-05-3, 2-((Trimethylsilyl)ethynyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 57963-08-3, 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 57963-08-3, name is 5,6-Dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Method E A mixture of TBTU (642 mg, 2.0 mmol), pyrazole-3-carboxylic acid or 5-chloro pyrazole-3-carboxylic acid (intermediate II) (1.0 mmol), the relevant arylamine (1.0 mmol), DIPEA (348 muL, 2.0 mmol) and DMAP (12 mg, 0.1 mmol) in dry DMF (5 mL) was stirred at 80 0C for 3 days. After cooling to rt the mixture was concentrated and hydrochloric acid (IM, 10 mL) was added. The mixture was extracted with EtOAc (4 x 10 mL) , the combined organic phases washed with NaCl (sat., aq.; 20 mL), dried (Na2SO4), concentrated and purified by chromatography (EtO Ac/heptane) to give the desired compound.

According to the analysis of related databases, 57963-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; WO2007/51981; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

Iminodibenzyl (50.0 g, 0.256 mol) was dissolved in DMF (700 mL), sodium hydride (12.3 g, 0.306 mol, 60% dispersion in oil) was slowly added in portions and the mixture was stirred at 50 C. for 2 h. Ethyl 3-bromopropionate (100 mL, 0.77 mol) was slowly added dropwise and the mixture was heated at reflux temperature overnight. The mixture was cooled and evaporated. The residue was suspended in DCM (150 mL), filtered and the solvent was evaporated. The resulting residue was purified in portions by column chromatography (silica gel, DCM) to give 5.1 g (7%) of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid ethyl ester.TLC: Rf=0.69 (silica gel, DCM).3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid ethyl ester (1.41 g, 4.77 mmol) was dissolved in ethanol (30 mL) and a solution of sodium hydroxide (0.75 g, 18.8 mmol) in water (5 mL) was added. The mixture was stirred for 3.5 h. 1 N Hydrochloric acid (17 mL) was added and the mixture was extracted with DCM (2×25 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4) and the solvent was evaporated to give 1.18 g (92%) of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid.Carbonyldiimidazole (0.33 g, 2.1 mmol) was dissolved in DCM (5 mL) and 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propionic acid (0.56 g, 2.1 mmol) was added. The mixture was stirred at room temperature for 1.5 h under a nitrogen atmosphere. Simultaneously, sodium methoxide (0.8 mL of a 30% solution in water, 4.4 mmol) was added to a solution of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.43 g, 2.2 mmol) in methanol (5 mL). The mixture was stirred at room temperature for 1.5 h under a nitrogen atmosphere. The solvent was evaporated and the residue was stripped with DCM (6 mL). The above solution of the activated carboxylic acid was added to the residue and the reaction mixture was stirred at room temperature overnight. Water (10 mL) was added followed by DCM (50 mL) and the phases were separated. The aqueous phase was extracted with DCM (20 mL) and the combined organic phases were dried (MgSO4). After evaporation of the solvent, the residue was purified by column chromatography (silica gel, 150 mL, methanol/ethyl acetate 1:5). Evaporation of the solvent afforded 0.41 g (52%) of the title compound as a solid.TLC: Rf=0.28 (silica gel, methanol/ethyl acetate 1:5). LC-MS: Calcd. for MH+: 373; found: 373.1H NMR (400 MHz, DMSO-d6, two rotamers, 1:1): delta2.49 (m, 1H), 2.60-2.72 (m, 3H), 3.07 (d, 4H), 3.47 (t, 1H), 3.86 (t, 1H), 4.08-4.20 (m, 2H), 4.22 (s, 1H), 4.62 (s, 1H), 6.90 (m, 2H), 7.01-7.16 (m, 6H), 7.40 (s, 0.5H), 7.45 (s, 0.5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 823-61-0, 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. 823-61-0, name is 3,6-Dimethyl-2-pyridinamine, molecular formula is C7H10N2, 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. 1-Amino-3,6-dimethylpyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate A solution of O-(mesitylsulfonyl)hydroxylamine (5.3 g, 24.6 mmol) in DCM (20 mL) was slowly added to a solution of 3,6-dimethylpyridin-2-amine (1.0 g, 8.2 mmol) in DCM (5 mL). A yellow precipitate was formed gradually, and after stirring for 1 h, the precipitate was collected by filtration and used for the next step without further purification. ESI MS: m/z 138 [M+H]+.

According to the analysis of related databases, 823-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunovion Pharmaceuticals Inc.; US2012/178748; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1083057-12-8, 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. 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, molecular formula is C17H19NO2, 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.

[00301] tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol).Water (0. 3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature inthe reactor below 45 C. After completion of the phthalic anhydride addition, the mixture washeated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/waqueous Na2S03 (1.5 eq) was added via addition funnel. After completion ofNa2S03 addition,the mixture was stirred for an additional30 min and the layers separated. The organic layer wasstirred and 10% wt/wt aqueous. Na2C03 (2 eq) was added. After stirring for 30 minutes, thelayers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organicphase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that was used directly in the next step.

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 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, Marinus, Jacobus; KARKARE, Radhika; MOORE, Michael, Douglas; WO2014/71122; (2014); 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. 52687-85-1, name is Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride, molecular formula is C7H7ClN2O, 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. category: pyridine-derivatives

The starting material can be manufactured as follows: A hot solution of 80 g (2 moles) of sodium hydroxide in 200 ml of water is added in portions, while stirring, to a mixture of 341 g (2 moles) of the hydrochloride of imidazo[1,2-a]pyridin-2(3H)-one in 700 ml of water. Then, a solution of 250.7 g (2.16 moles) of maleic acid in 600 ml of water is added dropwise in such a manner that the internal temperature of the reaction mixture remains between 40 and 45 C. After 30 hours at room temperature (20-25 C.) the mixture is cooled to 5 C., the resulting precipitate is filtered off, the filtrate is concentrated in vacuo to approximately half its volume, and the resulting product is filtered with suction. The combined residues are washed with a little cold methanol and dried in vacuo at 50 C. 400 g of 3-(1,2-dicarboxyethyl)-imidazo[1,2-a]pyridin-2(3H)-one having a melting point of 193 (decomposition) are obtained.

With the rapid development of chemical substances, we look forward to future research findings about 52687-85-1.

Reference:
Patent; Ciba-Geigy Corporation; US4426380; (1984); A;,
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.851386-40-8, name is 4-Chloro-2,5-difluoropyridine, molecular formula is C5H2ClF2N, molecular weight is 149.53, as common compound, the synthetic route is as follows.Safety of 4-Chloro-2,5-difluoropyridine

To a solution of 4-chloro-2,5-difluoropyridine (200 nig, 1.33 mmol) and 4M HCl in dioxane (0.33 ml, 1.33 mmol) in 2-propanol (3 ml) was added hydrazine hydrate (134 mg, 2.68 mmol). Reaction mixture was stirred at rt for 1 month. Solvents were evaporated under vacuum. Aqueous NaHC03 solution was added to the mixture. Precipitate formed was filtered oft” washed with water and dried under vacuum yielding 51 mg of 4-chloro-5- fluoro-2-hydrazinylpyridine and 2,5-difluoro-4-hydrazinylpyridine as a 1/1 mixture.MS: m/z 162 I M I f ] . 1H NMR (DMSO-d6) delta: 8. 19 (br s, IH), 8.09 (d, 1 1 1 ).. 7.70 (d, 1 1 1 }.. 7.66 (d, H), 6.88 (d, IH), 6.55 (d, IH), 4.39 (d, 2H), 4.21 (br s, 2H ) To a solution containing the mixture of 4-chloro-5-fluoro-2-hydrazinylpyridine and 2,5-difluoro-4-hydrazinylpyridine (50 mg, 0.31 mmol) in THF (3 ml) at 0C was added triphosgene (92 mg, 0.31 mmol). Reaction mixture was stirred at 0C for 1 hour. Solvents were evaporated under vacuum. A solution of IM aqueous HCl was then added and the mixture was extracted 3 times with EtOAc. Organic layers were concentrated under vacuum. Evaporation residue was dissolved in IM NaOH solution and extracted twice with EtOAc. Aqueous phase was acidified with cone, HCl and extracted twice with EtOAc. Organic layers were dried and concentrated under vacuum. Evaporation residue was stirred in Et20, filtered off and dried under vacuum yielding 1 1 mg of pure 7-chloro-6-fluoro- [l,2,4]triazolo[4,3-a]pyridii -3(2H)-one. MS: m/z 188 [M+Hf. 1H NMR ( DM SO-d,.) delta: 12.71 (br s, IH), 8.27 (dd, IH), 7.75 (dd, IH)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851386-40-8, 4-Chloro-2,5-difluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem