Tag: M.W:200-300

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

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.

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

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

Name is 3-Bromo-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 17965-71-8, its synthesis route is as follows.,17965-71-8

Example lb: Synthesis of 3-bromo-l,5-naphthyridine-5-oxide (C-3) [00306] 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 m-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 NaHCC>3 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). lR NMR (300 MHz, CDCI3- 6) delta: 9.21 (s, 1H), 9.01 (s, 1H), 8.52 (d, J = 6.3 Hz, 1H), 7.96 (d, J = 8.7 Hz, 1H), 7.53 (m, 1H); ESI-MS m/z : 208.10 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-1,5-naphthyridine

Reference£º
Patent; INTELLIKINE, LLC; REN, Pingda; LI, Liansheng; CHAN, Katrina; WO2013/78441; (2013); 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.,1309774-03-5

0540-1 A suspension of 7-bromo-2-chloro-1,5-naphthyridine (44 mg), 1-(4-aminopiperidin-1-yl)ethanone (26 mg), tris(dibenzylideneacetone)dipalladium(0) (15 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (30 mg), and sodium tert-butoxide (50 mg) in 1,4-dioxane (2 mL) was stirred at 80 C. for 4 hours. The reaction mixture was cooled to room temperature, and purified by silica gel column chromatography (methanol-ethyl acetate), thereby obtaining 1-(4-((6-chloro-1,5-naphthyridin-3-yl)amino)piperidin-1-yl)ethanone (8.1 mg). MS m/z (M+H): 305.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO449,mainly used in chemical industry, its synthesis route is as follows.,1309774-03-5

0370-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (300 mg), bis(pinacolato)diboron (469 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (100 mg), potassium acetate (241 mg), and 1,4-dioxane (12.3 mL) was stirred at 100 C. for 3 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate (557 mg), sodium carbonate (261 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (87 mg), and water (1.2 mL) were added thereto, followed by stirring at 110 C. for 1 hour. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane, chloroform-methanol), thereby obtaining tert-butyl 4-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (149 mg) as a white solid. MS m/z (M+H): 414.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine,belong naphthyridine compound

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, 7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5 its synthesis route is as follows.,1309774-03-5

Example 4b: Synthesis of 7-bromo-2-morpholino-l,5-naphthyridine F-32) [00336] A mixture of 7-bromo-2-chloro-l,5-naphthyridine (F-31) (200 mg, 0.82 mmol, 1.0 eq) and morpholine (10 mL) was stirred in a sealed-tube at 140 C overnight. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL) and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-morpholino- 1,5-naphthyridine (F-32) (180 mg, 74.7% yield). ESI-MS m/z : 294.01 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

Reference£º
Patent; INTELLIKINE, LLC; REN, Pingda; LI, Liansheng; CHAN, Katrina; WO2013/78441; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 4-Bromo-2,7-naphthyridin-1-amine, cas is 959558-28-2 its synthesis route is as follows.,959558-28-2

A solution of Bromo compound 6a (96 mg, 0.43 mmol, 1.2 equiv), Pd(PPh3)4 (10 mol%), CuI (5 mol%) and Triphenylphosphine (10 mg) in Triethylamine (1.5 mL, 10.8 mmol, 30 equiv) was de-oxygenated using steam of Argon gas. A de-oxygenated solution of alkyne 3b (150 mg, 0.36 mmol, 1 equiv) in DMF (4 mL) was added slowly over a period of 10 min to the solution and the reaction temperature was increased to 50 C and allowed to stir 12 h. The reaction was quenched by addition of NH4Cl (5 mL) at room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed with water (5 ¡Á 50 mL) and washed with brine (1 ¡Á 50 mL). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The pure product 15 was obtained by flash column chromatography. Yield = 49%.; TLC Rf = 0.1 (10 % MeOH/CH2Cl2). 1H NMR (500 MHz, DMSO-d6) delta 10.65 (s, 1H), 9.60 (s, 1H), 8.93 (s, 1H), 8.74 (d, J = 5.7 Hz, 1H), 8.48 (s, 1H), 8.39 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 8.5 Hz, 1H), 7.92 (s, 2H), 7.88 (d, J = 5.7 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 3.55 (s, 2H), 2.80 (s, 3H), 2.37 (s, 8H), 2.14 (s, 3H); 13C NMR (126 MHz, DMSO) delta 164.01, 162.28, 158.58, 152.20, 149.63, 148.92, 147.44, 140.37, 138.34, 137.81, 132.86, 131.74, 127.93, 127.77, 123.97, 118.86, 117.71, 117.37, 112.05, 101.07, 92.66, 90.47, 57.90, 55.19, 53.17, 46.19, 24.28; HRMS (ESI+): calcd. for C30H29F3N7O (MH+) 560.2380, found 560.2380

With the complex challenges of chemical substances, we look forward to future research findings about 4-Bromo-2,7-naphthyridin-1-amine

Reference£º
Article; Wang, Modi; Naganna; Sintim, Herman O.; Bioorganic Chemistry; vol. 90; (2019);,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 6-Amino-8-bromo-1,7-naphthyridine, and cas is 5912-35-6, its synthesis route is as follows.,5912-35-6

To a stirred solution of 8-BROMO- [1, 7] naphthyridin-6-ylamine (1.70 g) in a mixture of toluene (7 ml), DMF (11 ml) and aqueous K2CO3 (2.31 g in 5 ml water) is added bis (dibenzylideneacetone) palladium (174 mg), triphenylphosphine (158 mg) and 5-fluoro-2- methoxyphenylboronic acid (1.38 g). The mixture is stirred for 3.5 hours at 100C, then diluted with ethyl acetate and filtered through Celite. The ethyl acetate solution is washed with 2N NAOH and water, dried over magnesium sulphate, then concentrated to afford the title compound. MS: APCI 270.0 MH+.

With the complex challenges of chemical substances, we look forward to future research findings about 5912-35-6,belong naphthyridine compound

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/55013; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,3-Bromo-8-chloro-1,7-naphthyridine,1260670-05-0,Molecular formula: C8H4BrClN2,mainly used in chemical industry, its synthesis route is as follows.,1260670-05-0

To a solution of 3-bromo-8-chloro-1,7-naphthyridine (2.43g) in toluene (30 mL), EtOH (10 mL), and 10%Na 2CO 3 aq. (10 mL)pd (dppf) Cl 2. DCM (420 mg) was added. 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.1g) was added dropwise under N 2 protection. The mixture was allowed to stir at 100C for 16h. The reaction was quenched by H 2O (50 mL)and extracted by EtOAc for 3 times. Organic layer was combined and washed with brine. The resulting solution was concentrated and purified by silicagel (eluting with hexane-EtOAc using a gradient from 8: 1 to 5: 1) to afford 8-chloro-3-vinyl-1,7-naphthyridine (1.1g)as a brown solid. 88%).

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Bromo-8-chloro-1,7-naphthyridine,belong naphthyridine compound

Reference£º
Patent; BETTA PHARMACEUTICALS CO., LTD; ZHANG, Yao; WANG, Yiqian; FU, Bang; CHEN, Jie; WANG, Jiabing; DING, Lieming; (43 pag.)WO2020/15716; (2020); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

0032-1 1,4-Dioxane (2 mL) and a 2 mol/L sodium carbonate aqueous solution (315 muL) were added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (77 mg), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphino)dichloropalladium(II) (15 mg) in a nitrogen atmosphere, and the reaction vessel was sealed, followed by stirring at 100 C. for 5 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. 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. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate), thereby obtaining 2-chloro-7-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (57 mg) as a white solid. 1H-NMR (CDCl3) delta: 9.15 (1H, d, J=2.0 Hz), 8.35-8.31 (2H, m), 8.04 (1H, s), 8.00 (1H, s), 7.57 (1H, d, J=8.6 Hz), 5.53 (2H, s), 3.68-3.63 (2H, m), 0.99-0.93 (2H, m), 0.00 (9H, s)., 1309774-03-5

With the rapid development of chemical substances, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

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

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

Step 1 To a stirred solution of intermediate D-7 (200 mg, 0.45 mmol) and 3-bromo-8-chloro-l ,7- naphthyridine (165 mg, 0.68 mmol) in THF (8 mL) was added LHMDS (1 M in THF, 1.13 mL, 1.13 mmol) at RT. The mixture was stirred at 45 C for 2 h, then an additional 1 eq. of LHMDS was added and the mixture was stirred at 45 C overnight. The mixture was diluted with saturated Nu0 and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The resulting residue was rediluted with 5 mL of DCM and TFA (0.5 mL) was added. The resulting mixture was stirred at 25 C for 2 h, then neutralized with NaHC03, and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by prep-TLC (DCM: MeOH = 15 : 1) to afford compound L-1. MS for L-1 : m/e = 550 and 552 (M+l)., 1260670-05-0

With the rapid development of chemical substances, we look forward to future research findings about 3-Bromo-8-chloro-1,7-naphthyridine

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem