Tag: M.W:100-200

Synthetic Route of 53014-84-9, 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.53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, molecular weight is 121.1366, as common compound, the synthetic route is as follows.

INTERMEDIATE 552- [(Hydroxy)(6-methylpyridin-3-yl)methyll acrylic acid ethyl esterTo a solution of 6-methylpyridine-3-carbaldehyde (5.0 g, 41 mmol) in ethyl acrylate (10 mL) at room temperature was added DABCO (1.0 g, 9 mmol), and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (Si02, hexane to 40%> ethyl acetate), to give the title compound (5.6 g, 62%) as a yellow oil. LCMS (ES+) 222.2 (M+H)+, RT 0.98 minutes.

The chemical industry reduces the impact on the environment during synthesis 53014-84-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; PARTON, Andrew Harry; ALI, Mezher Hussein; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; FORD, Daniel James; FRANKLIN, Richard Jeremy; LANGHAM, Barry John; NEUSS, Judi Charlotte; QUINCEY, Joanna Rachel; WO2012/32334; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1822-51-1 , The common heterocyclic compound, 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

Reference Example 1 Methyl 2-(pyridin-4-yl)methoxybenzoate (Reference Compound 1-(1)) To a solution of methyl salicylate (10 g, 66 mmol) and 4-chloromethylpyridine hydrochloride (11 g, 67 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (19 g, 140 mmol) under ice-cooling, and then the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into an ice water and the aqueous layer was extracted with ethyl acetate (150 mL, twice). The ethyl acetate layer was washed with a saturated brine solution (200 mL), dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness, and the resultant residue was purified with a silica gel column chromatography (hexane/ethyl acetate) and dried to give 12 g (75 %) of the titled compound as a colorless solid. 1H-NMR (300MHz, CDCl3) delta 3.93 (s, 3H), 5.19(s, 2H), 6.97(d, J=8.3Hz, 1H), 7.04(t, J=7.5Hz, 1H), 7.43-7.50(m, 3H), 7.87(dd, J=7.9, 1.8Hz, 1H), 8.63(d, J=6.1Hz, 2H) The following Reference Compounds 1-(2) to (8) were obtained by a production method similar to that of Reference Compound 1-(1) using compounds selected from known compounds, 4-chloromethylquinoline (CAS#5632-17-7;) and 2-acetamido-4-methanesulfonyloxymethylpyridine (CAS#864461-12-1;) and commercially available compounds.

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2128156; (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.82454-61-3, name is 5-Ethynylpyridin-2-amine, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.Recommanded Product: 82454-61-3

A solution of 7 (36.0 g), copper(I) iodide (334 mg), bis-(triphenylphosphine)-palladium(II)-dichloride (557 mg), triphenylphosphine (414 mg) and triethylamine (25.5 mE) in MeTHF (145 mE) was treated at 70-75°C. within 2 to 3 hours with a MeTHF solution of 1.1 equiv. of 5-ethynylpyridin-2- ylamine (9) (prepared according to Example 11) and the resulting suspension was subsequently stirred at 70-75°C. for additional 5-10 hours. The mixture was cooled to 30° C. and treated with water (150 mE) and 25percent aqueous ammonium hydroxide solution (30 mE). The biphasic mixture was stirred for 30 minutes and the layers were then allowed to separate for 20 minutes. The aqueous layer was removed and the MeTHF layer was washed twice with a mixture of water (150 mE) and 25percent aqueous ammonium hydroxide solution (30 The MeTHF layer was subsequently washed with water (3x 150 mE). The organic layer was polish filtered, and the filtrate was treated with n-tributylphosphine (1.00 mE). MeTHF was then distilled off and completely replaced by isopropanol (500 mE in total) at atmospheric pressure. The resulting suspension (ca. 250 mE) was heated to reflux and stirred at reflux for 2 hours then cooled to room temperature overnight. The product was filtered and washed with two portions of isopropanol (50 mE). The wet crystals were dried at 50° C. and <30 mbar until constant weight affording 29.45 g (84percent yield based on 7) of compound A as red crystals with a purity of 99.7percent (HPEC, area-percent). At the same time, in my other blogs, there are other synthetic methods of this type of compound,82454-61-3, 5-Ethynylpyridin-2-amine, and friends who are interested can also refer to it. Reference:
Patent; Hoffmann-La Roche Inc; Bachmann, Stephan; Bailey, Daniel; Brice, Jodie; Cedilote, Miall; Dong, Zhiming; Hildbrand, Stefan; Miller, Doreen; Spurr, Paul; Srivastava, Amit; Wichmann, Juergen; Woltering, Thomas; Yang, Jason; Zhang, Pingsheng; US2013/85278; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16665-38-6, 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. 16665-38-6, name is (4-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, 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.

4-Methoxypyridine-2-carbaldehyde, used as starting material was prepared as follows:- Manganese(IV) oxide (2.412 mL, 139.42 mmol, 4eq) was added portionwise to (4- methoxypyridin-2-yl)methanol (4.85g, 34.85 mmol, leq) in ethyl acetate (15OmL). The resulting mixture was stirred at 80 0C for 2 h. The hot reaction mixture was filtered through celite. The resulting mixture was evaporated to dryness to afford desired A- methoxypyridine-2-carbaldehyde (3.01 g, 21.93 mmol, 62.9 %). IH NMR (400.132 MHz, DMSO) delta 3.93 (3H, s), 7.27 (IH, m), 7.44 (IH, d), 8.63 (IH, d), 9.96 (IH, s)

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 16665-38-6, (4-Methoxypyridin-2-yl)methanol.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/56886; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83282-46-6, Adding some certain compound to certain chemical reactions, such as: 83282-46-6, name is 3,6-Dimethylpicolinic acid,molecular formula is C8H9NO2, 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 83282-46-6.

Trimethylsilyldiazomethane 2M in ether (5.7 ml, 11.4 mmole, 1.4 eq.) is added dropwise at RT to a suspension of 3,6-dimethyl-pyridine-2-carboxylic acid (containing potassium chloride) (3.07 g a 25%, 8.12 mmole, 1 eq.) in benzene (24 ml) and methanol (8 ml), and the yellow suspension is stirred at RT for 1.5 h. The yellow mixture is diluted with ethyl actate, washed once with sat. aqueous sodium bicarbonate sol, once with water, once with brine, dried with magnesium sulfate and the solvents are removed in vacuo. Purification of the residue (914 mg) by chromatography on a 20 g Silicycle silica cartridge (eluent heptane / ethyl acetate 5 – 40% 20 min) affords 3,6-dimethyl-pyridine-2-carboxylic acid methyl ester (714 mg, 53.2%) as a colorless liquid.MS (m/e) = 166.3 [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. 83282-46-6, 3,6-Dimethylpicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALVAREZ SANCHEZ, Ruben; BLEICHER, Konrad; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RUDOLPH, Markus; WO2011/117264; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62068-78-4, 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.62068-78-4, name is 2,6-Dichloronicotinamide, molecular formula is C6H4Cl2N2O, molecular weight is 191.02, as common compound, the synthetic route is as follows.

To a stuffed solution of 2,6-dichloro-nicotinamide (500.00 mg; 2.62 mmol; 1.00 eq.) in DMF (5.00 ml; 10.00 V) was added 3-(4-hydroxy-phenoxy)-benzonitrile (670.16 mg; 3.14 mmol; 1.20 eq.) and cesium carbonate (1722.97 mg; 5.24 mmol; 2.00 eq.) at RT. The resulting reaction mixture was stirred for 5h. The reaction completion was confirmed by TLC. After completion of the reaction, the reaction mixture was quenched by the addition of water (20 mL). The solid was collected by filtration and dried under vacuum. The solid was further triturated with acetonitrile (25 mL) and filtered and dried under vacuum to afford 6-chloro-2-[4-(3-cyano- phenoxy)-phenoxy]-nicotinamide (800.00 mg; 83.6 %; off white solid). HPLC: 98.06% purity. MS: m/z = 364.0 [M+H].

The chemical industry reduces the impact on the environment during synthesis 62068-78-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; QIU, Hui; CALDWELL, Richard D.; NEAGU, Constantin; MOCHALKIN, Igor; LIU-BUJALSKI, Lesley; JONES, Reinaldo; TATE, Devon; JOHNSON, Theresa L.; GARDBERG, Anna; WO2015/61247; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 677728-92-6, 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 677728-92-6 as follows.

A suspension of 6-fluoro-pyridine-3-carbaldehyde (125 mg, 1.0 mmol), N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]- acetamide (200 mg, 0.746 mmol), K2CO3 (552 mg, 4.0 mmol) in acetonitrile (20 niL) was stirred at 60 C under nitrogen for 15 h. The reaction mixture was diluted with EtOAc, filtered and evaporated. The crude product was purified by flash chromatography (1 : 1 hexane/EtOAc followed by 1 % MeOH in EtOAc) to give the title product as oil (235 mg, 84 %). ESI MS m/z 31 A (M + H+); 1H NMR (400 MHz, CD3OD) delta 9.97 (s, 1 H), 8.60 (d, J= 2.0 Hz, 1 H), 8.29 (dd, J= 8.4, 2.4 Hz, 1 H), 7.70 (dd, J= 12.0, 1.6 Hz, 1 H), 7.33-7.20 (m, 3 H), 4.80-4.78 (m, 1 H), 4.19 (t, J= 9.0 Hz, 1 H), 3.85 (dd, J= 9.6, 6.4 Hz, 1 H), 3.58 (d, J= 4.8 Hz, 2 H), 1.97 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; WO2009/120789; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6200-60-8, Imidazo[1,2-a]pyridine-3-carboxylic acid, 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, Quality Control of Imidazo[1,2-a]pyridine-3-carboxylic acid, blongs to pyridine-derivatives compound. Quality Control of Imidazo[1,2-a]pyridine-3-carboxylic acid

General procedure: To a solution of 2-methyl-3-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine, Intermediate 1, (150 mg, 0.7 mmol) in dichloromethane (DCM) (5.0 mL) was added HATU (348 mg, 0.91 mmol), followed by DIPEA (0.6 mL, 3.5 mmol) and 1-naphthoic acid (222 mg, 1.3 mmol), and the mixture stirred at room temperature for 1 h. The reaction mixture was diluted with water and the aqueous layer extracted with DCM (*2). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase HPLC (Method A) to afford the title compound as a white solid (94 mg, 36% yield). MS (ESI): mass calcd. for C24H21N3O, 367.1; m/z found, 368.1 [M+H]+. 1H NMR (400 MHz, Methanol-d4) delta 8.12-7.93 (m, 2H), 7.89-7.74 (m, 1H), 7.67-7.35 (m, 9H), 5.20-4.92 (m, 2H), 4.46-4.22 (m, 1H), 4.13-3.98 (m, 0.3H), 3.76 (d, J=54.9 Hz, 3H), 3.52-3.41 (m, 1H), 2.93-2.75 (m, 0.7H), 2.57-2.30 (m, 1H).

The synthetic route of 6200-60-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); 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.97483-77-7, name is 5-Bromopicolinonitrile, molecular formula is C6H3BrN2, molecular weight is 183.01, as common compound, the synthetic route is as follows.Computed Properties of C6H3BrN2

Intermediate 10: 1-(5-Bromopyridin-2-yl)ethanone; See W098/46605; 5-Bromo-2-cyanopyridine (Markevitch, David Y. ; Rapta, Miroslav; Hecker, Scott J. ; Renau, Thomas E. ; Synth. Commun.; 33; 19; 2003; 3285 – 3290) (8 g, 43.7 mmol) was dissolved in dry THF (200 mL) and cooled to – 20C. Methylmagnesium bromide (43.7 mL, 3M) was added drop wise and the temperature was held between -20C and -10C for 3 hours. The reaction mixture was cooled to -40C and concentrated HCl (4.5 mL) in water (15 mL) was added dropwise. It was stirred for 10 minutes at -35C and then poured into a beaker with potassium phosphate buffer (300 mL, 1M, pH 7), under stirring. Ethyl acetate (300 mL) was added and the organic phase was dried over sodium sulfate. Upon concentration at room temperature under reduced pressure to – 50 mL the product crystallized, 2.4 g, mp 112C. The mother liquor was further concentrated and chromatographed on silica gel with dichloromethane/ ethylacetate (100:1) to give another 3.25 g product (65% combined yield). (at)H-NMR (DMSO-d(at)) No.: 2.60 (s, 3H) ; 7.88 (dd, 1H) ; 8.25 (dd, 1H) ; 8.86 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,97483-77-7, 5-Bromopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA UK LIMITED; WO2005/116023; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 170886-13-2, 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 170886-13-2, name is 2-(Trifluoromethyl)pyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

An alternative synthetic process is provided: A mixture of 2-(trifluoromethyl)pyridin-4-ol (5 g, 30.7 mmol), 3,4-difluorobenzaldehyde (4.36 g, 30.7 mmol) and potassium carbonate (8.47 g, 61.3 mmol) in Nu,Nu-dimethylformamide (DMF) (30 mL) was sealed and heated under microwave at 110 C for 3 h. Then the reaction mixture was cooled, and concentrated in vacuo. The concentrate was purified via Biotage column (Hexane/EtOAc 100% to 3/1) to afford the title compound (6.4 g, 37.6%) as a white solid. LCMS (ESI): m/z 286 [M + H]+; 1.35 min (ret time)

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 170886-13-2, 2-(Trifluoromethyl)pyridin-4-ol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; SANG, Yingxia; WAN, Zehong; ZHANG, Qing; WO2014/114694; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem