1309774-03-5 | Page 8 of 11 | Heterocyclic Building Blocks-Naphthyridine

Brief introduction of 1309774-03-5

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1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0157-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), 5-methoxypyridine-3-amine (25 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (24 mg), and cesium carbonate (33 mg) in 1,4-dioxane (1 mL) was stirred at 140 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 6-chloro-N-(5-methoxypyridin-3-yl)-1,5-naphthyridine-3-amine (5.4 mg). MS m/z (M+H): 287.

1309774-03-5, The synthetic route of 1309774-03-5 has been constantly updated, and we look forward to future research findings.

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

Downstream synthetic route of 1309774-03-5

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1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1309774-03-5

0398-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), bis(pinacolato)diboron (62 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (16 mg), potassium acetate (40 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 3-(4-Iodo-1H-pyrazol-1-yl)pyridine (61 mg), sodium carbonate (43 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (17 mg), and water (0.2 mL) were added thereto, followed by stirring at 80 C. for 8 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-hexane), thereby obtaining 2-chloro-7-(1-(pyridin-3-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine (27 mg). MS m/z (M+H): 308.

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Analyzing the synthesis route of 1309774-03-5

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,1309774-03-5

0386-2> A mixture of 7-bromo-2-chloro-1,5-naphthyridine (182 mg), bis(pinacolato)diboron (286 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (61 mg), potassium acetate (147 mg), and 1,4-dioxane (4 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 3-Ethyl-4-iodo-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole (250 mg), sodium carbonate (158 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (53 mg), and water (0.4 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 2-chloro-7-(3-ethyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (161 mg). MS m/z (M+H): 370.

The synthetic route of 1309774-03-5 has been constantly updated, and we look forward to future research findings.

Some tips on 1309774-03-5

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.

New learning discoveries about 1309774-03-5

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Example 0646 0646-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (5.0 g), 1-tert-butoxycarbonyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (6.04 g), sodium carbonate (4.4 g), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropallad

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Some tips on 1309774-03-5

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.

0393-3 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (80 mg), 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (231 mg), sodium carbonate (87 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (23 mg), water (0.3 mL), and 1,4-dioxane (3 mL) was stirred at 80 C. for 2 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-hexane), thereby obtaining 7-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-1H-pyrazol-4-yl)-2-chloro-1,5-naphthyridine (76 mg). MS m/z (M+H): 389.

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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).

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Downstream synthetic route of 1309774-03-5

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1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0385-7 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (142 mg), bis(pinacolato)diboron (223 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (47 mg), potassium acetate (115 mg), and 1,4-dioxane (3 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(3-(3-ethyl-4-iodo-1H-pyrazol-1-yl)propyl)morpholine (204 mg), sodium carbonate (124 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (41 mg), and water (0.3 mL) were added thereto, followed by stirring at 80 C. for 4 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-ethyl-1H-pyrazol-1-yl)propyl)morpholine (18 mg). MS m/z (M+H): 386., 1309774-03-5

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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.

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Simple exploration of 1309774-03-5

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.

1309774-03-5, 7-Bromo-2-chloro-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1309774-03-5

Example 0623 0623-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (50 mg), tert-butyl carbamate (32 mg), tris(dibenzylideneacetone)dipalladium(0) (18 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (23 mg), cesium carbonate (187 mg), and 1,4-dioxane (4 mL) was stirred at 120 C. for 9 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining tert-butyl (6-chloro-1,5-naphthyridin-3-yl)carbamate (47 mg). MS m/z (M+H): 280.

1309774-03-5 7-Bromo-2-chloro-1,5-naphthyridine 58310544, anaphthyridine compound, is more and more widely used in various fields.