Category: pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 603301-02-6, name is 7-Bromofuro[3,2-c]pyridin-4(5H)-one. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

227.1 7-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-one DIAD (4.91 mmol, 992 mg) was added dropwise to PPh3 (753 mg, 2.80 mmol) in 20 mL of THF. The mixture was stirred for 30 min. Then 7-bromofuro[3,2-c]pyridine-4(5H)-one (300 mg, 1.402 mmol) was added followed by the addition of 2-(quinolin-2-yl)ethanol (243 mg, 1.402 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was extracted with water/ethyl acetate. The organic phase was extracted with 1N HCl. The acidic aqueous phase was basified with 1N NaOH and extracted with DCM. The organic phase was extracted with water, dried over MgSO4, filtered, concentrated and purified by chromatography to give the title compound as white solid (119 mg, 23%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 603301-02-6, 7-Bromofuro[3,2-c]pyridin-4(5H)-one.

Reference:
Patent; AbbVie Inc.; Abbott GmbH & Co. KG; Geneste, Herve; OCHSE, Michael; DRESCHER, Karla; TURNER, Sean; BEHL, Berthold; LAPLANCHE, Loic; DINGES, Juergen; JAKOB, Clarissa; BLACK, Lawrence; US2013/116233; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 861673-68-9, name is 2-(2-(tert-Butyl)phenoxy)pyridin-3-amine. A new synthetic method of this compound is introduced below., name: 2-(2-(tert-Butyl)phenoxy)pyridin-3-amine

A solution of 2-(2-tert-butylphenoxy)pyridin-3-amine (342 mg, 1.41 mmol) in dry THF (5 mL) was cooled at 0 C. and treated successively with n-BuLi (1.6M, 0.89 mL, 1.42 mmol) and chloropyrazine (90 mg, 0.79 mmol). After stirring at 23 C. for 24 h, the reaction was diluted with AcOEt. The organic solution was washed with H2O, dried (MgSO4) and concentrated to give crude material. Purification by flash chromatography (silica, CH2Cl2) provided Example 216 (40 mg, 16%) as a yellow foam. (M+H)+=320; 1H NMR (400 MHz, CDCl3) delta ppm 1.43 (s, 9 H), 7.00 (dd, J=7.8, 1.3 Hz, 1 H), 7.04 (dd, J=8.1, 5.0 Hz, 1 H), 7.37 (dt, J=7.3, 1.3 Hz, 1 H), 7.25 (dd, J=7.9, 1.8 Hz, 1 H), 7.29 (bs, 1 H), 7.50 (dd, J=8.1, 1.8 Hz, 1H), 7.82 (dd, J=5.1, 1.8 Hz, 1 H), 8.11 (bs, 1 H), 8.24 (bs, 1 H), 8.84 (dd, J=8.1, 1.8 Hz, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 861673-68-9, 2-(2-(tert-Butyl)phenoxy)pyridin-3-amine.

Reference:
Patent; Sutton, James C.; Pi, Zulan; Ruel, Rejean; L’Heureux, Alexandre; Thibeault, Carl; Lam, Patrick Y. S.; US2006/173002; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 71701-92-3, 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 71701-92-3 as follows.

n-BuLi (1.57M solution in hexane; 64 mL, 0.10 mol) is added dropwise to a solution of 3- bromo-2-chloro-5-trifluoromethylpyridine (20.00 g, 0.077 mol), DMF (7.72 mL, 0.10 mol) in toluene (400 mL) at -65C. After stirring at the same temperature for 30 min, the mixture is quenched by addition of 1 N HCI and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give crude 2-chloro-5-trifluorornethylpyridine-3-carbardehyde.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71701-92-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/58961; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 846021-26-9 ,Some common heterocyclic compound, 846021-26-9, molecular formula is C7H8N2O2, 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.

A mixture of 2-Amino-6-methyl-1licotinic acid (1.44 g, 9.46 mmol) and formamide (8.0 g, 178 mmol) was stirred at 170C for 2 hours. After cooling, the mixture was quenched with water (4 mL). The precipitate was filtered, washed with water and dried to afford 7-Methyl-pyrido [2,3-d] pyrimidin-4-ol (0.79g, 51%). 1H NMR (CDC13, 400 MHz) 8 8.49 (d, J=8.4Hz, 1H), 8.22 (s, 1H), 7.35 (d, J=8. 0Hz, 1H), 2.75 (s, 3H). MS (APCI+) [M+H] +162.

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. 846021-26-9, 2-Amino-6-methylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
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.56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.Quality Control of (6-Methylpyridin-3-yl)methanamine

Into a round bottom flask were combined 5-formyl-4′-methylbiphenyl-3-carboxylic acid(3.00 g, 12.5 mmol), (6-methylpyridin-3-yl)methanamine (1.91 g, 15.6 mmol), NN-diisopropylethylamine (6.46 g, 49.9 mmol) and NN-dimethylformamide (97 mL). NN,N’,N’-Tetramethyl-O-(7-azabenzotriazol- l-yl)uronium hexafluorophosphate (9.50 g, 25.0 mmol) was added in one portion and the mixture was heated at 60 0C for 2 h. After cooling, the mixture was poured onto saturated sodium bicarbonate (200 mL) and extracted with ethyl acetate (3 x 100 mL). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using methylene chloride:methanol gradient (0-10%) to afford the title compound. LC-MS: 346.2 [M+l ]+; 1H NMR (400 MHz, DMSO-d6): 10.14 (s, IH), 8.46-8.43 (m, 2H), 8.37-8.33 (m, 2H), 7.72 (d, 2H, J = 8.0 Hz), 7.64 (dd, IH, J = 8.0 Hz), 7.34 (d, 2H, J = 7.9 Hz), 7.22 (d, 2H, J = 7.9 Hz), 4.51 (d, 2H, J = 5.9 Hz), 2.44 (s, 3H), 2.37 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56622-54-9, (6-Methylpyridin-3-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 847902-56-1 ,Some common heterocyclic compound, 847902-56-1, molecular formula is C5H3FN2O3, 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.

Example 8A 2-Amino-5-fluoropyridin-3-ol 5.6 g of 5-fluoro-2-nitropyridin-3-ol (Example 7A; 36 mmol) were dissolved in 2 l of ethanol, a catalytic amount of palladium on activated carbon (10%) was added and the mixture was hydrogenated under standard hydrogen pressure for 16 h. The mixture was filtered off through silica gel and the filtrate was concentrated (product batch 1). The filter cake was rinsed with methanol until the colour of the filtrate was no longer yellowish. The filtrate was concentrated, giving a second product batch. This gave 4.26 g (85% of theory) of the title compound. LC-MS (Method 2): Rt=0.17 min MS (ESpos): m/z=128.9 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=5.4 (br. s, 2H); 6.8 (dd, 1H); 7.4 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847902-56-1, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; FOLLMANN, Markus; HARTUNG, Ingo; BUCHGRABER, Philipp; JAUTELAT, Rolf; HAssFELD, Jorma; LINDNER, Niels; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER, Eva-Maria; KNORR, Andreas; US2014/128372; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 720666-45-5, 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.720666-45-5, name is 2-Chloro-5-methoxypyridin-3-amine, molecular formula is C6H7ClN2O, molecular weight is 158.5856, as common compound, the synthetic route is as follows.

Example 1 4-(2-CHLORO-5-METHOXYPYRIDIN-3-YLAMINO)-3-CYANO-6-METHOXY- 7- (3-morpholinopropoxy) quinoline Sodium hexamethyldisilazane (1M solution in THF ; 0.76 ml) was added dropwise to a mixture of 3-AMINO-2-CHLORO-5-METHOXYPYRIDINE (0.05 g), 4-chloro-3-cyano- 6-METHOXY-7- (3-MORPHOLINOPROPOXY) quinoline (J. Med. CHEM., 2001,44, 3965-3977 & US Patent No. 6,002, 008; 0.125 g), DMF (2 ml) and THF (5 ml) that had been cooled to 0 C. The mixture was stirred at 0 C for 5 minutes and at ambient temperature for 1 hour. Acetic acid (0.052 ml) was added and the resultant mixture was concentrated by the evaporation of the THF. Solid material was removed by filtration and washed with DMF (2 ml). The resultant concentrate and DMF washings were combined and injected directly on to a Waters Symmetry column (CIS reversed-phase, 5 microns, 19 mm diameter, 100 mm length) and eluted with decreasingly polar mixtures of water (containing 5% methanol and 1% acetic acid) and acetonitrile. The material so obtained was mixed with methylene chloride (20 ml) that contained 5% methanol. Potassium carbonate (0.5 g) was added and the mixture was stirred at ambient temperature for 10 minutes. The solids were filtered off and the filtrate was evaporated. The resultant residue was triturated under diethyl ether. There was thus obtained the title compound as a solid (0.099 g); NMR Spectrum: (CDC13) 2.13 (m, 2H), 2.48 (m, 4H), 2.57 (t, 2H), 3.73 (m, 4H), 3.74 (s, 3H), 3.81 (s, 3H), 4.29 (t, 2H), 6.58 (s, 1H), 6.73 (br s, 1H), 6.9 (s, 1H), 7.48 (s, 1H), 7.81 (s, 1H), 8.78 (s, 1H); Mass Spectrum: M+HS 484 and 486. The 3-AMINO-2-CHLORO-5-METHOXYPYRIDINE used as a starting material were prepared as follows:- A solution of hydrogen peroxide (30% aqueous solution; 4.6 ml) in water (5 ml) was added dropwise (approximately 0.05 ml/minute) to a solution of 3-AMINO-5-METHOXYPYRIDINE (Y. Tamura et AL., J. Org. Chem. , 1981,46, 3564; 3.8 g) in 12N aqueous hydrochloric acid (60 ml) that was heated to 70 C and the resultant mixture was stirred and heated to 70 C for 30 minutes. The mixture was cooled to ambient temperature and the precipitate was isolated. The solid so obtained was 3-amino-2,6-dichloro-5-methoxypyridine (0.165 g). The filtrate was cooled to 0 C and the acidity of the solution was reduced to pH4 by the addition of ION aqueous potassium hydroxide solution. The resultant solution was extracted with methylene chloride and the organic layer was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 4: 1 mixture of petroleum ether (b. p. 40-60 C) and diethyl ether as eluent. There was thus obtained 3-amino- 2-chloro-5-methoxypyridine as a white solid (1.3 g); NMR Spectrum: (CDC13) 3.81 (s, 3H), 4.08 (m, 2H), 6.6 (s, 1H), 7.51 (s, 1H) ; Mass Spectrum: M+H 159. On further elution using a 2: 1 mixture of petroleum ether (b. p. 40-60 C) and diethyl ether, there was obtained as a solid a second portion (0.342 g) of 3-amino-2,6-dichloro-5-methoxypyridine ; NMR Spectrum: (CDC13) 3.86 (s, 3H), 4.12 (m, 2H), 6.65 (s, 1H) ; Mass Spectrum: M+H+ 193.

The chemical industry reduces the impact on the environment during synthesis 720666-45-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/69827; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16063-69-7, 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 16063-69-7 as follows.

2,4,6-Trichloropyridine (20.0 g, 190.63 mmol) was dissolved ethanol (100 mL). Methyl amine (33% wt in ethanol, 81.9 mL, 657 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2 weeks. The white precipitate was filtered off and washed with te/t-butylmethylester and water to give (2,6-dichloro- pyhdin-4-yl)-methylamine (11.9 g, 61 %) as a white crystalline compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16063-69-7, its application will become more common.

Reference:
Patent; NeuroSearch A/S; WO2008/92942; (2008); A2;,
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.10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H8N2, molecular weight is 120.15, as common compound, the synthetic route is as follows.Recommanded Product: 10592-27-5

Step 2; A solution of Br2 (2.78 ml, 8.64 g, 54 mmole) in dry dichloromethane (40 ml) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-10C) solution of 2.3-dihydro-1H-pyrrolo[2,3-b]pyridine (6.5 g,54 mmole) in a mixture of dry dichloromethane (60 ml) and pyridine (6 ml). The suspension was stirred at 0C for 2 hrs, poured into a mixture of NaHCO3 (120 ml) and saturated aqueous Na2S2O3 (15 ml) and extracted with a solution of ethyl acetate/methanol (3X200 ml). The organic layers were concentrated to afford 3.7 g of 5-bromo- 2,3-dihydro- 1H-pyrrolo[2,3-b]pyridine (2) after purification by flash chromatography using dichloromethane as eluent (35% yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.98 ( t, J = 8.54 Hz, 2H ) 3.48 (t, J=8.55 Hz, 2H) 6.58 (bs, 1 H) 7.37(s,1 H) 7.71 (s,1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; EP2070928; (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.603310-75-4, name is 5-Isopropylpyridin-2-amine, molecular formula is C8H12N2, molecular weight is 136.1943, as common compound, the synthetic route is as follows.Quality Control of 5-Isopropylpyridin-2-amine

General procedure: To the solution of Acid SM-IX (750 mg, 2.i8 mmol, iOO mol-%) in dry DCM (iO ml) under nitrogen atmosphere was added 3-amino-5- methylisoxazole (427 mg, 4.36 mmol, 200 mol-%) and pyridine (526 p1, 6.53mmol, 300 mol-%). T3P (50 w-% in EtOAc) (2.6 ml, 4.36 mmol, 200 mol-%) was added dropwise and the reaction mixture stirred at rt for four hours. DCM (i 0 ml) and i 0 % NaH 003 (30 ml) were added. The water phase was extracted twice with DCM (2 x iO ml). The organic phases were combined and washed with 0.i N HCI solution (3 x 30 ml), water (3 x 30 ml) and finally withbrine (3 x 30 ml) and dried with sodium sulfate. The crude yield of compound i was 95 % (875 mg).1H NMR (200 MHz, DMSO-d6): 0.97 (5, 3 H), i.24 -2.46 (m, i6 H),2.37 (5, 3H), 2.58 – 3.Oi (m, 2 H), 6.64 (5, i H), 6.88-7.06 (m, i H), 7.07 – 7.25 (m, 2 H), iO.88 (5, i H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,603310-75-4, 5-Isopropylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; FORENDO PHARMA LTD; HIRVELAe, Leena; HAKOLA, Marjo; LINNANEN, Tero; KOSKIMIES, Pasi; STJERNSCHANTZ, Camilla; (182 pag.)WO2018/224736; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem