Heterocyclic Building Blocks-Naphthyridine

17965-71-8, 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. 3-Bromo-1,5-naphthyridine, cas is 17965-71-8,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Example 1.1.1 and Example 1.1.2: 3-Bromo-[1,5]naphthyridine-5-oxide and 3-bromo-1,5-naphthyridine-1-oxide [Show Image] [Show Image] 4.43 g (21.2 mmol, 1 eq) of 3-bromo-1,5-naphthyridine (W. Czuba, Recueil des Travaux Chimiques des Pays-Bas 1963, 82, 988-996) were introduced in 165 mL of methylene chloride. 5.23 g (21.2 mmol, 1 eq) of meta-chloroperbenzoic acid were then added portionwise at 0 C. The mixture was stirred at rt for 18 h. The mixture was washed with 1M aqueous NaOH solution and water. Organic layer was dried over Na2SO4, 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 3.08 g of 3-bromo-1,5-naphthyridine-5-oxide (pale yellow powder) with 64% yield and 1.00 g of 3-bromo-1,5-naphthyridine-1-oxide (yellow powder) with 21 % yield.3-Bromo-[1,5]naphthyridine-5-oxide Yield: 3.08 g (64 % of theory). m.p.: 148-149 C. 1H-NMR (DMSO-d6, 400 MHz): delta.= 9,21 (d, 1H); 9,10 (d, 1H); 8,75 (d, 1H); 8,06 (d, 1H); 7,80 (dd, 1H) ppm. MS: m/z 226 (M+H+).3-Bromo-[1,5]naphthyridine-1-oxide Yield: 1.00 g (21 % of theory). m.p.: 153-154 C. 1H-NMR (DMSO-d6, 400 MHz): delta= 9,12 (d, 1H); 9,03 (s, 1H); 8,86 (d,1H); 8,36 (s, 1H); 7,94 (dd, 1H) ppm. MS: m/z 226 (M+H+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17965-71-8, 3-Bromo-1,5-naphthyridine

Reference£º
Patent; Aeterna Zentaris GmbH; EP2332939; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 1,6-Naphthyridin-5(6H)-one, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 23616-31-1, its synthesis route is as follows.

[0622] A suspension of XI-3 (2.36 g, 15.7 mmol, 1 eq), N-bromosuccinimide (3.1 g, 17.3 mmol, 1 eq), and 50 mL of 1,2-dichloroethane was stirred at rt for 3.5 hrs. The mixture was filtered; the solids were washed successively with small amounts of chloroform, water, and diethyl ether, and then dried to leave XI-4 (0.8 g, 23percent yield). MS (ESI) m/z (M+H)+ 226.8.

23616-31-1, 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.,23616-31-1 ,1,6-Naphthyridin-5(6H)-one, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
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10261-82-2, 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. 1,5-Naphthyridin-2(1H)-one, cas is 10261-82-2,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A 250 mL round bottomed flask charged with 1,5-naphthyridin-2(1H)-one (2.98 g, 20.37 mmol) and phosphorus oxychloride (40 ml, 437 mmol) was heated at 100 C. for 3 h. The reaction was cooled to room temperature and excess POCl3 was removed in vacuo. The residue was poured onto ice and neutralized with NaHCO3. The mixture was extracted with DCM (4*) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (ISCO (80 gram)) eluting with EtOAc:DCM (0:1?1:4) to give 1.08 g (32%, 2 steps) of a light-yellow amorphous solid. ESI-MS 164.9, 166.9 [M+1].

The chemical industry reduces the impact on the environment during synthesis,10261-82-2,1,5-Naphthyridin-2(1H)-one,I believe this compound will play a more active role in future production and life.

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;,
1,8-Naphthyridine – Wikipedia
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Name is 1,5-Naphthyridin-2(1H)-one, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 10261-82-2, its synthesis route is as follows.

To a suspension of Intermediate 3 (5.9 g) in dry DME (180 ml) and dry DMF (45 ml) at 0C under argon was added in portions NaH (60% w:w dispersion in mineral oil, 3.2 g). After stirring for 45 minutes, the mixture was treated with lithium bromide (8.8 g) and the suspension was allowed to warm to room temperature. After stirring for 45 minutes, the mixture was treated with allyl bromide (7 ml) and then stirred at 65C for 3 h. The mixture was cooled to room temperature and concentrated under reduced pressure, then t-BuOMe (300 ml) was added and the mixture was then washed with 1 N NH4Cl (200 ml). The combined aqueous phases were extracted with t-BuOMe (2 x 100 ml). The organic phases were combined, washed with brine (200 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (4.29 g, 57%). To obtain an additional amount of the desired compound, the combined aqueous phases were extracted exhaustively with CH2Cl2. Then, the organic extracts were combined, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (1.5 g, 20%). [ES MS] m/z 187 (MH+).

10261-82-2, 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.,10261-82-2 ,1,5-Naphthyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; GLAXO GROUP LIMITED; EP2080761; (2009); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

17965-71-8, 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. 3-Bromo-1,5-naphthyridine, cas is 17965-71-8,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-bromo-l,5-naphthyridine (C-2) (35.6 g, 170 mmol, 1.0 eq) in dichloromethane (300 mL) at 0C was added w-chloroperbenzoic acid (35.27 g, 204 mmol, 1.2 eq) in portions. The resulting mixture was stirred for lh at RT. The reaction was complete based on TLC analysis. The reaction mixture was washed with saturated Na2S03 solution and saturated NaHC03 solution sequentially, and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (1-5% MeOH-DCM) to afford the desired product 3-bromo-l,5-naphthyridine-5-oxide (C-3) (28.35 g, 74% yield). ‘H NMR (300 MHz, CDCl3-Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2011/149937; (2011); 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.

0001-4 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (30 mg), 1-(3-morpholinopropyl)-1H-pyrazole-4-boronic acid pinacol ester (59 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (5 mg) and sodium carbonate (20 mg) in 1,4-dioxane (1.9 mL) and water (0.1 mL) was stirred at 100 C. for 7.5 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, ethanol (4 mL) was added thereto, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-ethyl acetate, NH silica), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)propyl)morpholine (45.6 mg) as a white solid. MS m/z (M+H): 358.

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

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.

c) (EVtert-butyl 3-(7-oxo-7.8-dihvdro-l ,,8-naphtfayridin-3-yr)acrylate; A reaction vessel was charged with 6-bromo-l,8-naphthyridin-2(lH)-one (1.5g, 6.69 mmol), tert-bxyl acrylate (4.86 mL, 33.45 mmol), and (J-Pr)2EtN (3.5 niL, 20.07 mmol) followed by DMF (40 mL). The solution was de-oxygenated with argon for 20 min. The mixture was treated with Pd(OAc)2 (150 mg, 0.67 mmol) and P(o-tol)3 (407 mg, 1.34 mmol) then heated to 100 0C for 15 h (overnight). A TLC anlaysis indicated that only the starting arylhalide is present. At this time the mixture was a yellow suspension. To this mixture was added 20 DMSO (20 mL) and an additional 75 mg OfPd(OAc)2. The mixture was heated at 100 0C for 24 h. After cooling, the dark mixture was filtered through celite and the filter cake was rinsed with EtOAc (100 mL). The filtrate was extracted with EtOAc (2 x 100 mL). The combined organic fractions were washed with brine (2 x 100 mL), H2O (100 mL), dried over MgSO4 and filtered through a pad of silica gel. The filtrate was concentrated to about 50 mL then treated with about 150 mL hexanes to form a precipitate. The precipitate was filtered to give the product as a light brown solid. Yield: 700 mg(39%); 1H-NMR (300 MHz, DMSO-d6) delta 12.36 (s, IH), 8.83 (d, IH, J = 2.3 Hz), 8.53 (d, IH, J = 2.3 Hz), 7.89 (d, IH, J = 9.0 Hz), 7.64 (d, IH, J = 18.0 Hz), 6.65 (d, IH, J = 18.0 Hz), 6.62 (m, IH)5 1.51 (s, 9H); ESIMS m/z 273 [Ci5H16N2O3 + H]+

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; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, 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. Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH.

The chemical industry reduces the impact on the environment during synthesis,100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
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.

0494-1 A suspension of 7-bromo-2-chloro-1,5-naphthyridine (1.22 g), 5-isopropylpyridazine-3-amine (755 mg), and potassium tert-butoxide (1.23 g) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 1 hour. After ethyl acetate and water were added to the reaction mixture, the organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Toluene was added to the obtained residue, and the solid matter was collected by filtration, thereby obtaining 7-bromo-N-(5-isopropylpyridazin-3-yl)-1,5-naphthyridine-2-amine (0.92 g) as a white solid. MS m/z (M+H): 346.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7-Bromo-2-chloro-1,5-naphthyridine, 1309774-03-5

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

It is a common heterocyclic compound, the naphthyridine compound, 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7 its synthesis route is as follows.

General procedure: (Method C4) Synthesis of N’-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine In a 20 mL sealed tube was dissolved 8-chloro-3-methoxy-1,5-naphthyridine (70 mg, 360 mumol) in DMF (2.00 mL). To this was added N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine (124 mg, 396 mumol) and the reaction mixture was stirred at 70 C. for 17 h. Upon cooling to RT, the mixture was dissolved in DMF and purified using Gilson reverse phase chromatography. The product fractions were combined, concentrated and the resulting crude was extracted into DCM, washed 1* sodium carbonate, 1*H2O, dried with Na2SO4, filtered through fritted funnel, concentrated to yield N1-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as light yellow solid. MS [M+H]=471.0; Calc’d 470.5 for C29H22N60.

952059-69-7, 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.,952059-69-7 ,8-Chloro-3-methoxy-1,5-naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem