72754-05-3 | Page 3 of 3 | Heterocyclic Building Blocks-Naphthyridine

Share a compound : 6-Bromo-1,8-naphthyridin-2-ol

As the rapid development of chemical substances, we look forward to future research findings about 72754-05-3

6-Bromo-1,8-naphthyridin-2-ol, cas is 72754-05-3, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

72754-05-3, Example 7 Synthesis of boronic acid 7Reaction reagents and conditions: a. 1 ) NaH, THF, r.t.; 2) nBuLi, B(OiPr)3, -70C to 0C7.1 Boronic acid 7: To a solution of compound 6 (10 g, 44.44 mmol) in dry tetrahydrofuran (350 mL) was added sodium hydride(2 g, 66.66 mmol, 80% dispersion) at 0C. After the mixture was stirred at room temperature for 30 min, the mixture was cooled below -60C in a dry ice/acetone bath, and n- butyllithium (70 mL, 112 mmol, 1.6 M in hexane) was added over 30 min. The mixture was kept stirring for another 30 min, then triisopropyl borate (40 mL, 177 mmol) was added dropwise. The reaction mixture was stirred for 10 min, and then warmed to 0C slowly in an ice bath. HC1 (5 N) was added to the mixture to adjust pH = 3-4, and the mixture was stirred for 20 min. Aq. NaOH was added to the mixture to adjust pH = 10. After filtration, the organic layer was separated. The aqueous layer was extracted with a mixture of ethyl acetate/THF (4/1; 2 x 120 mL) and EtOAc (100 mL) . The aqueous layer was adjusted to pH = 5-6 with HC1. The precipitate thus formed was collected by filtration and dried to give boronic acid 7 (3.5 g, 41%) a white solid.

As the rapid development of chemical substances, we look forward to future research findings about 72754-05-3

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; WO2013/29548; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Some tips on 72754-05-3

72754-05-3 6-Bromo-1,8-naphthyridin-2-ol 12520144, anaphthyridine compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.72754-05-3,6-Bromo-1,8-naphthyridin-2-ol,as a common compound, the synthetic route is as follows.,72754-05-3

A mixture of 6-bromo-lH-l, 8-naphthyridin-2-one (1 equiv, which was prepared as per prepared as per- 1.3), Pd (PPh3)2Cl2 (0.1 equiv), Cul (0.15 equiv), (i-Pr)2EtN (4 equiv) in DMF (15 times) was deoxygenated with nitrogen for 15 minutes. Then vinyl trimethyl silane (2 equiv) was added and heated to 125C for lOh. The reaction was monitored by thin layer chromatography. Filtered through a pad of silica gel at room temperature. The filtrate was concentrated and the residue was purified by silica gel chromatography (eluted with 20 to 30% ethyl acetate/hexane) to provide the title compound as a solid (30% yield). ESI MS m/z -245.22(M+H)+.

72754-05-3 6-Bromo-1,8-naphthyridin-2-ol 12520144, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; GAMPA, Venugopala Krishna; GANGANAMONI, Srinivasulu; SIRIGIREDDY, Balakrishna Reddy; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2015/186137; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Application of 7-Chloro-1,8-naphthyridin-2-ol

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The naphthyridine compound, cas is 72754-05-3 name is 6-Bromo-1,8-naphthyridin-2-ol, mainly used in chemical industry, its synthesis route is as follows.

72754-05-3, 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]+

As the rapid development of chemical substances, we look forward to future research findings about 72754-05-3

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

Analyzing the synthesis route of 72754-05-3

The synthetic route of 72754-05-3 has been constantly updated, and we look forward to future research findings.

Step 1: A mixture of 6-bromo-i,8-naphthyridin-2(1H)-one (1.0 equiv) and 2,5-dihydrofuran (10 equiv) in AcOH (0.05 M) was irradiated with UVA lamps (Rayonet reactor, RPR3 500 A bulbs) at RT overnight. The mixture was filtered, washing with EtOAc, and the solids were dried in vacuo. The so-obtained residue was purified via flash chromatography over silica gel, eluting with DCM and 0-20% EtOAc gradient to provide the title (rac)-2-bromo- 6a,6b,7,9,9a,9b-hexahydrofuro[3 ?,4?: 3 ,4]cyclobuta[ 1,2-c] [1 ,8]naphthyridin-6(5H)-one as a yellow solid in 9% yield. ?H NIVIR (400 IVIHz, DMSO-d6) oe 10.60 (s, 1H), 8.20 (m, 1H), 7.85 (m, 1H), 4.13 (d,J= 9.4 Hz, 1H), 3.97 (d,J= 9.6 Hz, 1H), 3.38 (m, 3H), 3.06 (d,J 8.9, 5.1 Hz, 1H), 2.90 (dd, J= 9.7, 4.4 Hz, 1H), 2.84 (m, 1H). LCMS (m/z) (M+H) = 295.1/297.1, Rt = 0.69 mm.

The synthetic route of 72754-05-3 has been constantly updated, and we look forward to future research findings.

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