Category: pyridine-derivatives

Synthetic Route of 609-71-2, Adding some certain compound to certain chemical reactions, such as: 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid,molecular formula is C6H5NO3, 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 609-71-2.

A stirred suspension of NaH 60% dispersion in mineral oil (206 mg, 5.14 mmol), washed twice with distilled n-hexane and once with Et20 in 2 mL of anhydrous DMF under N2 atmosphere was treated dropwise with a solution containing the 2-hydroxynicotinic acid (600 mg, 4.31 mmol) in 5 mL of anhydrous DMF. The mixture was left under stirring at room temperature for 2h and then 3,4-difluoro-benzylbromide (1.06 g, 5.14 mmol) was added and the mixture stirred and heated at 50C for 1 6h. After the mixture was concentrated under reduced pressure and the residue was treated with water to give a solid, which was collected by vacuum filtration. Next the solid was refluxed for 4h in aq. 10% NaOH (10 mL) and the resulting mixture was cooled and made acid with 1 N aq.HCI. The white solid formed was collected by filtration and washed with nhexane and Et20, giving the derivative 3.9 as white solid (857 mg, 3.23 mmol, 75% yield).1HNMR (400 MHz, DMSO-d6): 65.30 (5, 2H, CH2); 6.78 (t, 1H, J = 6.9 Hz, Ar);7.22-7.24 (m, 1H, Ar); 7.41 -7.53 (m, 2H, Ar); 8.41 (d, 2H, J = 6.9 Hz, Ar) ppm.Anal. Calcd for C13H9NO3F2: C, 58,87%; H, 3.42%; N, 5.28%; Found: C, 58,99%; H, 3.47%; N, 5.43%

According to the analysis of related databases, 609-71-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (63 pag.)WO2016/198597; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 88511-27-7, Adding some certain compound to certain chemical reactions, such as: 88511-27-7, name is 4-Amino-3-iodopyridine,molecular formula is C5H5IN2, 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 88511-27-7.

To a solution of 4-aminopyridine (1a, 37.65 g, 0.4 mole) in HOAc (200 mL) was added iodine monchloride (130 g, 0.8 mole) portionwise. The reaction mixture was stirred at 45 C. for 20 h, then diluted with water (500 mL). The mixture was cooled to 0 C., and basified 30% NaOH to pH=9-10. The solution was extracted with EtOAc (1 L×2) and the combined extracts were washed with 15% Na2S2O3 (400 mL×2), water, brine, dried over Na2SO4, and evaporated in vacuo to give 1b (62 g) as a light yellow solid. ES-MS m/z 221 (MH+). [0185] Into a pressure flask was added 1b (4.4 g, 20 mmol), cupric iodide (228 mg, 1.2 mmol), (trimethylsilyl)acetylene (7.08 g, 72 mmol), triethylamine (200 mL) and DMF (80 mL). The mixture was stirred under nitrogen for 10 min, followed by addition of Pd(PPh3)2Cl2 (0.84 g, 1.2 mmol). The mixture was then stirred to 70 C. for 5 h, and then diluted with ethyl acetate (600 mL). The solution was washed with H2O (250 mL×2), brine (250 mL), dried over Na2SO4, and evaporated in vacuo to give crude product which was purified by flash chromatography (100% CH2Cl2 to 2% MeOH in CH2Cl2) to afford Compound 1c (2. 97 g, 78%) as a light brown solid. 1H NMR (CDCl3) delta 8.37 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 6.53 (d, J=5.6 Hz, 1H), 4.67 (bs, 2H), 0.27 (s, 9H). ES-MS m/z 191 (MH+). [0186] Into an ice-cold solution of 1c (1.35 g, 7.1 mmol) in THF (50 mL) was added 95% NaH (1.86 g, 8.5 mmol). The mixture was stirred at 0 C. for 10 min, rt for 10 min, then cooled back to 0 C. (Boc)2O (1.86 g, 8.5 mmol) was added and the mixture was stirred at 0 C. for 30 min and then rt for 2 h. Additional 95% NaH (0.08 g, 3.5 mmol) and (Boc)2O (0.2 g, 0.92 mmol) were added and the mixture was stirred at rt for another 2 h. The reaction was then quenched slowly with saturated NaHCO3 (10 mL), extracted with ethyl acetate (200 mL×2). The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (EtOAc/hexane; 1:3) to give 1d (0.67 g). ES-MS m/z 219 (MH+). [0187] To a solution of 1d (1.3 g, 4.5 mmol) in DMF (20 mL) was added cupric iodide (0.85 g, 4.5 mmol). The mixture was stirred at 80 C. for 6 h and then filtered. The filtrate was extracted with ethyl acetate (100 mL×3), and the organic layer was washed with H2O, brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (Ethyl acetate/hexane; 1:3) to give Compound 1e (0.25 g, 26%). 1H NMR (CDCl3) delta 8.89 (s, 1H), 8.47 (d, J=5.8 Hz, 1H), 7.98 (d, J=5.7 Hz, 1H), 7.62 (d, J=3.7 Hz, 1H), 6.66 (d, J=3.7 Hz, 1H), 1.69 (s, 9H). ES-MS m/z 219 (MH+). [0188] To a solution of 1e (0.178 g, 0.82 mmol) in methylene chloride (5 mL) was added TFA (1.0 mL) slowly. The mixture was stirred at rt for 1.5 h, and The solvent was evaporated to obtain 5-azaindole 1f as a white solid (0.18 g, 95%). 1H NMR (CDCl3) delta 8.97 (s, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.35 (d, J=5.7 Hz, 1H), 7.29 (m, 1H), 6.68 (d, J=3.3 Hz, 1H). ES-MS m/z 119 (MH+). [0189] A mixture of Compound 1f (0.26 g, 2.2 mmol) and cesium carbonate (1.43 g, 4.4 mmol) in DMF (10 mL) was stirred at rt for 10 min, and then 3-methoxypropylbromide (0.40 g, 2.64 mmol) was added. The reaction mixture was stirred at 60 C. for 3 h. The solvent was evaporated and the residue was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with water (3×50 mL), brine (2×50 mL), then dried (Na2SO4) and evaporated in vacuo to give a brown oil. The crude product was purified by flash column chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1g (0.26 g, 62%) as light brown oil. 1H NMR (CDCl3) delta 8.91 (s, 1H), 8.31 (d, J=5.8 Hz, 1H), 7.27 (s, 1H), 7.11 (d, J=3.2 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 4.25 (t, J=6.7 Hz, 2H), 3.32 (s, 3H), 3.25 (t, J=5.7 Hz, 2H), 2.05 (m, 2H). ES-MS m/z 191(MH+). [0190] Oxalyl chloride (3 mL) was added slowly to a solution of compound 1g (0.22 g, 1.14 mmol) in ether (5 mL). The mixture was heated to 48 C. in a pressure tube overnight. TLC shown that some starting materials were still present. Additional 0.5 mL of oxalyl chloride was added and stirring was continuted at 48 C. for another night. The mixture was then cooled down to rt, to which methanol (3 mL) was added. The mixture was heated to 48 C. and stirred for 2 h. The volatiles removed under vacuo and the residue was purified by flash chromatography (from 100% DCM to DCM/MeOH/NH4OH; 97:3:0.3) to afford Compound 1h (0.15 g, 48%) as a white solid. 1H NMR (CDCl3) delta 8.51 (d, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.37 (m, 1H), 4.34 (t, J=6.8 Hz, 2H), 3.97 (s, 3H), 3.35 (s, 3H), 3.30 (t, J=5.7 Hz, 2H), 2.12 (m, 2H). ES-MS m/z 277 (MH+). [0191] The alpha-ketoester Compound 1h (53.8 mg, 0.20 mmol) and amide Compound 1i (23 mg, 0.14 mmol) were combined in dry THF (3 mL) under argon and cooled with an ice bath as a solution of 1.0 M potassium t-butoxide in THF (1 mL, 1 mmol) was added dropwise. The mixture was stirred at 0 C. for 30 …

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. 88511-27-7, 4-Amino-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Han-Cheng; Maryanoff, Bruce E.; Ye, Hong; US2004/192718; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1207557-36-5, 6-Bromo-4-methoxypyrazolo[1,5-a]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, Recommanded Product: 1207557-36-5, blongs to pyridine-derivatives compound. Recommanded Product: 1207557-36-5

To a solution of 6-bromo-4-methoxypyrazolo[i,5-a]pyridine (Intermediate P1; 2.00g, 227.1 mmol) and 1 -methyl-4- (4,4, 5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (2.02 g, 208.1 mmol) in dioxane (10 mL) was added 2 M Na2CO3(aq) (8.1 mL, 17.6 mmol) and Pd(PPh3)4 (4.584 g, 3.967 mmol). The reaction mixture was purged with nitrogen for 2 mm, sealed and heated at 90 C for 4 h. After cooling to ambient temperature, the reaction mixture was diluted with water (50 mL) and stirred for 30 mm. The resulting suspension was vacuum filtered, rinsed sequentially with water (2 x 20 mL) and Et20 (2 x 10 mL) to yield the crude title compound, which was used in the next step without further purification. MS (apci), m/z = 229.1 (M+H).

The synthetic route of 1207557-36-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31181-79-0, (3-Fluoropyrid-2-yl)methanol, 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, Product Details of 31181-79-0, blongs to pyridine-derivatives compound. Product Details of 31181-79-0

Preparation 60; 2-Chloromethyl-3-fluoro-pyridine EPO Dissolve (3-fluoro-pyridin-2-yl)-methanol (215 mg, 1.69 mmol) in dichloromethane (10 mL) and cool to 0 0C. Add thionyl chloride (160 muL, 2.20 mmol) and stir the reaction for one hour. Add dichloromethane (50 mL) and stir the reaction with saturated aqueous sodium bicarbonate (2 x 40 mL) and brine (2 x 40 mL). Separate and dry the organic portion over magnesium sulfate, filter, and concentrate under reduced pressure to provide 198 mg (80%) of product, which is used without further purification. MS: m/z 146, 148 [C6H5ClFN + I]+; 1H NMR (300 MHz, CDCl3): delta 8.41-8.44 (m, IH), 7.41-7.47 (m, IH), 7.28-7.34 (m, IH), 4.75 (d, J = 2.0 Hz, 2H); 19F NMR (282 MHz, CDCl3): delta -123.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,31181-79-0, (3-Fluoropyrid-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 70298-88-3, name is 2,2-Dimehtyl-N-pyridin-3-yl-propionamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

In the three bottle,3-Pivalamidopyridine (20.0 g, 112.2 mmol) was dissolved in anhydrous tetrahydrofuran (200 mL).In nitrogen protection, the temperature drops to -78 C,N-butyllithium (17.8 g, 280.5 mmol) was added dropwise and the solution was dropped.Slowly warming to 0C for 3 hours,Then cool down to -78 C,N-methyl-N-methoxyacetamide (17.4 g, 168.3 mmol) was added dropwise.After completion of the dropwise addition, the reaction was slowly warmed to room temperature for 10 h.After the reaction was completed, the reaction was quenched with 1N hydrochloric acid, extracted with ethyl acetate (100 mL×3), and the organic phase was collected and washed with saturated brine (100 mL×1).The solvent was evaporated under reduced pressure to give crude N-(4-ethanhydrin-3-yl)trimethylacetamide.The crude product was applied on a silica gel column (mobile phase: PE_EA=5:1) to obtain 11.2 g of a pure product with a yield of 45.4%.

With the rapid development of chemical substances, we look forward to future research findings about 70298-88-3.

Reference:
Patent; Guizhou University; Liu Li; Huang Zhuyan; Yue Yi; (8 pag.)CN107382839; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1513-66-2, 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 1513-66-2, name is 2,3-Difluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 18 A mixture of A17 (60 mg, 0.10 mmol), 2,3 -difluoropyri dine (24 mg, 0.21 mmol) and Cs2C03 (101 mg, 0.308 mmol) in DMSO (1 mL) was stirred at 65C for 2 h. The mixture was diluted with water (30 mL) and extracted with EtOAc (3 x 25 mL). The combined organic layers were dried over Na2S04 and filtered to afford the crude product of A18, which was used in the next step directly without further purification.

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 1513-66-2, 2,3-Difluoropyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; DAI, Xing; (84 pag.)WO2017/139210; (2017); 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.1060811-62-2, name is 4,6-Dichloronicotinaldehyde, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.Formula: C6H3Cl2NO

A pre-mixed stirred solution of compound 3 (7.4 g, 42.28 mmol) in dichloromethane (40 mL) containing triethyl amine (11.37 mL, 84.56 mmol) was added ethyl mercaptoacetate (5.59 mL, 50.74 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 h and then to 50 °C for 18 h. The reaction mixture was quenched with water and extracted with ethyl acetate. After usual standard work up procedure and purification by column chromatography (silica gel: 100-200 mesh, eluent: 5percent ethyl acetate in pet ether) isolated compound 4; Light Yellow solid; Yield: 5.7 g, 56 percent; m.p.: 108-112 °C. Elemental analysis of C10H8NO2SCl calcd. (found) percent: C 49.69 (49.71), H 3.34 (3.32), N 5.80 (5.77)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060811-62-2, 4,6-Dichloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Sree Lakshmana Rao; Basaveswara Rao, Mandava V.; Prasad; Asian Journal of Chemistry; vol. 31; 3; (2019); p. 627 – 632;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84249-14-9, Adding some certain compound to certain chemical reactions, such as: 84249-14-9, name is 2-Amino-4-bromopyridine,molecular formula is C5H5BrN2, 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 84249-14-9.

To a stirred solution of 2-amino-4-bromopyridine (1.0 g, 5.78 mmol) in 1,4-dioxane (2 ml) was added K3PO4 (2.45 g, 11.56 mmol) and l,r-bis(di-tert-butylphosphino)ferrocene (0.168 g, 0.29 mmol) at rt. The reaction was purged with nitrogen for 30 min before adding phenylboronic acid (1.05 g, 8.67 mmol) and Pd(OAc)2 (0.065 g, 0.29 mmol) at rt. The reaction mixture was heated at 80C for 16 h. The resulting reaction mixture was cooled to rt, poured into water (50 ml) and extracted with EtOAc (3 x 25 ml). The combined organic phase was washed with water (25 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (62% EtOAc in hexane) yielding 4-phenylpyridin-2-amine (0.42 g, 2.47 mmol). LCMS: Method C, 1.47 min, MS: ES+ 171.14; NMR (400 MHz, DMSO-d6) delta ppm 7.96 (d, J=5.2 Hz, 1 H), 7.63 – 7.65 (m, 2 H), 7.41 – 7.52 (m, 3 H), 6.77 (dd, J=1.6 Hz, 5.2 Hz, 1 H), 6.69 (d, J=1.2 Hz, 1 H), 6.00 (s, 2 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. 84249-14-9, 2-Amino-4-bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D.; (109 pag.)WO2017/141036; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 171178-46-4, 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. 171178-46-4, name is 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid, molecular formula is C11H13ClN2O4, 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.

[00480] To a stirred solution of 5-tert-butoxycarbonylamino-2-chloro-isonicotinic acid (crude, 8.0 g) in methanol (50 mL) was added H2SO4 (5.0 mL). The mixture was then heated to reflux overnight. The reaction was cooled to room temperature and was concentrated in vacuum. The residue was diluted with water. The aqueous mixture was neutralized with sat. NaHCC>3 to pH = 8 and extracted with EA (100 mL x2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04 and filtered. The filtrate was evaporated in vacuum to residue, which was purified by silica gel

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 171178-46-4, 5-((tert-Butoxycarbonyl)amino)-2-chloroisonicotinic acid.

Reference:
Patent; HEDRICK Michael P.; HERSHBERGER Paul M.; MALONEY Patrick R.; PEDDIBHOTLA Satyamaheshwar; PINKERTON Anthony B.; WO2015/200534; A2; (2015);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74115-12-1, 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. 74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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.

7-((Difluoromethyl)sulfonyl)-4- fluoro-2,3-dihydrospiro[indene-l ,2′-[l,3]dioxolane] (3.0 g, 9.7 mmol) was combined with 5- chloropyridin-3-ol (1.89 g, 14.6 mmol) and sodium bicarbonate (2.45 g, 29.2 mmol) then the solids were suspended in N-methylpyrrolidinone (28.5 mL). The mixture was heated to 90 C for 14 hours then stirred at ambient temperature for 34 hours. The reaction mixture was diluted with ethyl acetate and water and the layers were separated. The aqueous was washed with ethyl acetate and the combined organic layers were washed five times with water, saturated NaCl, dried over Na2S04 and concentrated in vacuo to a cream-colored solid (4.36 g). LCMS ESI (+) m z (Mu+Eta) 418, 420.

According to the analysis of related databases, 74115-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; WO2015/35223; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem