Heterocyclic Building Blocks-Naphthyridine

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

2-methyl-1,8-naphthyridine (288 mg, 2 mmol) and twice the equimolar amount of selenium dioxide (221.92 mg-443.84 mg, 2 mmol-4 mmol) was dissolved in 50 ml of 1,4-dioxane under nitrogen or without nitrogen protection at 80 ¡ã C to 130 ¡ã C for 8-16 hours. During the reaction, the silica gel plate was detected at any time until the basic reaction of 2-methyl-1,8-naphthyridine was completed and a new point was generated. After completion of the reaction, the reaction mixture was suspended, purified on silica gel column with dichloromethane to obtain 1,8-naphthyridine-2-aldehyde., 1569-16-0

With the rapid development of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY, CHINESE ACADEMY OF SCIENCES; FU, WENFU; ZHAO, CHUNCHAO; (14 pag.)CN104974181; (2017); B;,
1,8-Naphthyridine – Wikipedia
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Name is 2-Methyl[1,8]-Naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0

In a 25 mL microwave reaction tube,Adding 2-methylnaphthyridine,Salicylaldehyde 0.5 g (4 mmol) and 10 ml acetic anhydride,Forming an orange-red solution,At a controlled temperature of 130 ¡ã C,Microwave power 50W, microwave reaction 40min,With the thin layer of the reaction process to monitor;After the reaction,The solvent was concentrated under reduced pressure to remove acetic anhydride,Oil-like viscous liquid,Dissolved with hot ethanol,Then recrystallized from acetone,Precipitation of yellow powder,That is, 2- (2′-hydroxystyryl) naphthyridine probe reagent,Yield 35percent.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; Guizhou University; Ceng, Xi; Ruan, Qin; Mou, Lan; Li, Zhao; Zhang, Hong; (29 pag.)CN106045996; (2016); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-8-chloro-1,7-naphthyridine, and cas is 1260670-05-0, its synthesis route is as follows.,1260670-05-0

Ammonium hydroxide (40 mL, 1.04 mol, 28%) was added to a solution of 3-bromo- 8-chloro-l,7-naphthyridine (1.00 g, 4.11 mmol) and THF (10 mL) in a sealed tube. The mixture was sealed, stirred at 100 C overnight, diluted with H20 (100 mL), and then extracted with EtOAc (3 x50 mL). The combined organic layers were washed (2x 100 mL brine), dried (Na2S04), filtered, and concentrated to dryness to give Intermediate 9 (824 mg, 89%) as a yellow solid. 1H NMR (400MHz, DMSO-i): delta 8.81 (s, 1H), 8.51 (s, 1H), 7.90 (d, 1H), 7.05 (br s, 2H), 6.87 (d, 1H); MS: 223.9 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about 1260670-05-0,belong naphthyridine compound

Reference£º
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (167 pag.)WO2018/170167; (2018); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Chloro-1,8-naphthyridine, cas is 15936-10-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

2-chloro-1,8-naphthyridine (89 mg, 0.54 mmol), 5-(trans-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (100 mg, 0.431 mmol), and cesium carbonate (202 mg, 0.620 mmol) were suspended in dry dimethylformamide (0.86 mL) under nitrogen and heated to 100 C. for 18 h. The mixture was cooled and extracted with ethyl acetate and water. The phases were separated and the organic was dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using the ISCO (0-100% EtOAc in hexane), gave the desired 5-(trans-3-((1,8-naphthyridin-2-yl)amino)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (32 mg, 0.089 mmol, 21% yield) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) delta: ppm 1.45 (s, 6H) 2.42 (ddd, J=13.88, 9.28, 3.29 Hz, 2H) 3.44-3.62 (m, 2H) 5.22-5.38 (m, 2H) 6.71 (d, J=8.92 Hz, 1H) 7.16 (dd, J=7.82, 4.46 Hz, 1H) 7.79-7.98 (m, 2H) 8.11 (q, J=3.12 Hz, 2H) 8.84 (dd, J=4.38, 1.90 Hz, 1H)., 15936-10-4

15936-10-4 is used more and more widely, we look forward to future research findings about 2-Chloro-1,8-naphthyridine

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
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1,8-Naphthyridine | C8H6N2 – PubChem

72754-05-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6-Bromo-1,8-naphthyridin-2-ol, cas is 72754-05-3,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Step 1: To a stirred solution of 6-bromo-1,8-naphthyridin-2(1H)-one (1 equiv) in DIVIF (0.2 M) at 25 C were added cesium carbonate (1.3 equiv) and iodoethane (1.1 equiv) and the reaction was stirred for 30 mm. The mixture was poured onto water and extracted three times with ethyl acetate. The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated to give 6-bromo-1-ethyl-1,8-naphthyridin-2(1H)-one as a yellow solid in 87% yield, which was used without further purification. LCMS (m/z) (M+H) = 253.0/255.0, Rt = 0.91 mm

The chemical industry reduces the impact on the environment during synthesis,72754-05-3,6-Bromo-1,8-naphthyridin-2-ol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 7-Bromo-2-chloro-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1309774-03-5, its synthesis route is as follows.

Example 3.1 : 7-Bromo-[1 ,5]naphthyridin-2-ylamineIn a sealed reactor, 500 mg (1 .23 mmol, 1 eq) of 7-bromo-2-chloro-1 ,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C.1H-NMR (DMSO-d6, 400 MHz): delta = 8,57 (d, 1 H); 8,05 (d, 1 H); 7,96 (d, 1 H); 6,04 (d, 1 H); 6,98 (s, 2H) ppm.MS: m/z 225 (M+H+).

1309774-03-5, 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.,1309774-03-5 ,7-Bromo-2-chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; AeTERNA ZENTARIS GMBH; WO2011/64250; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 5,7-Dichloro-1,6-naphthyridine, and cas is 337958-60-8, its synthesis route is as follows.

Intermediate 16: 1,1-Dimethylethyl (3S)-3-{[(7-chloro-1,6-naphthyridin-5-yl)oxy]methyl}-3-fluoro-1-piperidinecarboxylate[0413]1,1-dimethylethyl (3S)-3-fluoro-3-(hydroxymethyl)-1-piperidinecarboxylate (1.406 g, 6.03 mmol) in DMF (20 ml) was added sodium hydride (0.313 g, 7.84 mmol) (60% dispersion in mineral oil). This was stirred for 15 min before adding 5,7-dichloro-1,6-naphthyridine (1.2 g, 6.03 mmol). This was warmed to room temp and stirred for 4 h. The reaction had gone to completion and so was cautiously quenched with aqueous ammonium chloride before partitioning between aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and concentrated in vacuo to give the crude product. This was dissolved in DCM and purified through silica (50 g), eluting with a gradient of 0-50% ethyl acetate in DCM. Appropriate fractions were concentrated in vacuo to yield the title compound as a cream foamy gum (1.91 g).[0415]LCMS: Rt=1.18 min, MH+=395.85

337958-60-8, 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.,337958-60-8 ,5,7-Dichloro-1,6-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew; US2013/40984; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 7-Bromo-2-chloro-1,5-naphthyridine, and cas is 1309774-03-5, its synthesis route is as follows.

0390-7 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (29 mg), bis(pinacolato)diboron (36 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (10 mg), potassium acetate (23 mg), and 1,4-dioxane (1 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(3-(4-iodo-3-propyl-1H-pyrazol-1-yl)propyl)morpholine (43 mg), sodium carbonate (25 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (8 mg), and water (0.1 mL) were added thereto, followed by stirring at 80 C. for 3 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-3-propyl-1H-pyrazol-1-yl)propyl)morpholine (11 mg). MS m/z (M+H): 400.

1309774-03-5, 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.,1309774-03-5 ,7-Bromo-2-chloro-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 3-Bromo-8-chloro-1,7-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1260670-05-0, its synthesis route is as follows.

General procedure: To a set of vials containing the requisite aryl halide(0.15 mmol) was added a solution of Bi (30 mg, 0.073 mmol) in THF (1.0 mL). The vials werecapped and transferred into a glove box under an atmosphere of nitrogen. To each vial was then added a solution of LHMDS (1.0 M in THF). The mixtures were then heated at 50 C with stirring overnight. After that time, water (2 mL) and DCM (2 mL) were added to each vial. The mixtures were transferred to a set of fritted barrel filters. The organic layer from each vialwas drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. To each vial was then added DCM (1 mL) and TFA (0.5 mL). The mixtures were stirred at RT for 2 hours. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) andfiltered. The crude products were purified by mass triggered preparative HPLC [Waters Sunfire C18 column, Sum, 19×100 mm, using a gradient from 10% initial to 40% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 mm run timej to afford Examples 22-23.

1260670-05-0, 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.,1260670-05-0 ,3-Bromo-8-chloro-1,7-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; MERCK SHARP & DOHME CORP.; SCOTT, Jack, D.; BLIZZARD, Timothy, A.; WALSH, Shawn, P.; CUMMING, Jared, N.; (105 pag.)WO2017/95759; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1309774-03-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Example 0757 0757-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (600 mg), 1,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (442 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (174 mg), sodium carbonate (522 mg), 1,4-dioxane (24 mL), and water (2.4 mL) was stirred at 100 C. for 3 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The reaction residue was purified by silica gel column chromatography (chloroform-methanol, NH silica), thereby obtaining 2-chloro-7-(1,3-dimethyl-1H-pyrazol-4-yl)-1,5-naphthyridine (412 mg) as a white solid. MS m/z (M+H): 259.

The chemical industry reduces the impact on the environment during synthesis,1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem