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

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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

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 0929 N,N-dimethylacetamide (75 mL), 5-isopropylpyridazine-3-amine (5.12 g) and sodium tert-amyl oxide (9.08 g) were added to 7-bromo-2-chloro-1,5-naphthyridine (9.58 g), followed by stirring at 80 C. for 1 hour. The reaction mixture was poured into water (300 mL), and the precipitated solid was collected by filtration and washed with ethanol, thereby obtaining 7-bromo-N-(5-isopropylpyridazin-3-yl)-1,5-naphthyridine-2-amine (7.70 g) as a brown solid. 1H-NMR (DMSO-d6) delta: 10.89 (1H, s), 8.88 (1H, d, J=2.0 Hz), 8.80 (1H, d, J=2.0 Hz), 8.73 (1H, d, J=2.0 Hz), 8.48 (1H, d, J=2.0 Hz), 8.27 (1H, d, J=9.2 Hz), 7.79 (1H, d, J=9.2 Hz), 3.09-3.00 (1H, m), 1.32 (6H, d, J=6.6 Hz). MS m/z (M+H): 344.

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

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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.

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.

0421-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (48 mg), bis(pinacolato)diboron (58 mg), a 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride-dichloromethane complex (16 mg), potassium acetate (42 mg), and 1,4-dioxane (1.9 mL) was stirred at 100 C. for 2 hours. N-(4-bromopyridin-2-yl)acetamide (42 mg), sodium carbonate (45 mg), a bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (14 mg), 1,4-dioxane (0.3 mL), and water (0.19 mL)) were added to the reaction mixture, followed by stirring at 100 C. for 2 hours. The reaction mixture was cooled to room temperature, and purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining N-(4-(6-chloro-1,5-naphthyridin-3-yl)pyridin-2-yl)acetamide (12.6 mg) as a pale brown solid. MS m/z (M+H): 299.

Introduction of a new synthetic route about 1309774-03-5

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.

In a sealed tube, a mixture of 7-bromo-2-chloro-1,5-naphthyridine 4b (2.50 g, 10.3 mmol) and 28% aqueous ammonia solution (60 mL) in dioxane (60 mL) was heated at 140 C for 24 h. Then, the reaction mixture was allowed to cool at room temperature and water was added. The aqueous layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtrated and the solvent was removed under reduced pressure. The crude mixture was purified by column chromatography on silica gel eluting with dichloromethane, then dichloromethane/ethanol 98:2 to give compound 5 as a white solid (1.95 g, 85%); Rf=0.39 (CH2Cl2/EtOH, 96:4); mp: 168-169 C; 1H NMR (400 MHz, [D6]DMSO): delta=8.57 (d, J=2.1 Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.96 (d, J=9.1 Hz, 1H), 6.98 (br s, 2H), 6.04 (d, J=9.1 Hz, 1H); 13C NMR (100 MHz, [D6]DMSO): delta= 159.1, 145.1, 144.2, 138.6, 137.7, 133.8, 119.6, 116.9; MS (ESI) m/z (%): 224.0 (100) [M+H]+, 226.1 (100) [M+H+2]+.

Reference£º
Article; Defaux, Julien; Antoine, Maud; Loge, Cedric; Le Borgne, Marc; Schuster, Tilmann; Seipelt, Irene; Aicher, Babette; Teifel, Michael; Guenther, Eckhard; Gerlach, Matthias; Marchand, Pascal; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3748 – 3752;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Brief introduction of 1309774-03-5

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.

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.

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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.

0391-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (79 mg), bis(pinacolato)diboron (99 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (26 mg), potassium acetate (64 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-Iodo-3-propyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole (113 mg), sodium carbonate (69 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (23 mg), and water (0.2 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-propyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (53 mg). MS m/z (M+H): 384.

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1309774-03-5 is used more and more widely, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

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.

1309774-03-5, 0156-8 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (56 mg), bis(pinacolato)diboron (87 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (19 mg), and potassium acetate (45 mg) in 1,4-dioxane (2 mL) was stirred at 100 C. for 2 hours in a nitrogen atmosphere. 4-Iodo-3-methyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole (73 mg), sodium carbonate (49 mg), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (16 mg) were added to the reaction mixture, followed by stirring at 100 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, NH silica), thereby obtaining 2-chloro-7-(3-methyl-1-(3-(pyrrolidin-1-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine (13 mg). MS m/z (M+H): 356.

1309774-03-5 is used more and more widely, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

Some tips on 7-Bromo-2-chloro-1,5-naphthyridine

With the complex challenges of chemical substances, we look forward to future research findings about 1309774-03-5,belong naphthyridine compound

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.,1309774-03-5

0155-1 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 N2,N7-bis(5-methoxypyridin-3-yl)-1,5-naphthyridine-2,7-diamine (15 mg). 1H-NMR(CDCl3/CD3OD=4/1) delta: 8.44 (1H, d, J=2.7 Hz), 8.37 (2H, brs), 8.07 (1H, d, J=2.7 Hz), 7.99 (1H, d, J=9.0 Hz), 7.88 (2H, brs), 7.21 (2H, brs), 7.02 (1H, d, J=9.0 Hz), 3.91 (3H, s), 3.89 (3H, s). MS m/z (M+H): 375.

With the complex challenges of chemical substances, we look forward to future research findings about 1309774-03-5,belong naphthyridine compound

Some tips on 1309774-03-5

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.

0375-2 1,4-Dioxane (2 mL)/water (0.2 mL) was added to a mixture of 7-bromo-2-chloro-1,5-naphthyridine (75 mg), 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (105 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (21 mg), and sodium carbonate (65 mg), followed by stirring at 100 C. for 2 hours. After the reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the filter cake was washed with ethyl acetate. The filtrate and the washings were combined, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane, methanol-ethyl acetate, NH silica), thereby obtaining 2-chloro-7-(1-(pyridin-2-ylmethyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (64 mg) as a yellow solid. MS m/z (M+H): 322.

Introduction of a new synthetic route about 1309774-03-5

0399-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (48 mg), bis(pinacolato)diboron (60 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (16 mg), potassium acetate (39 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(4-Iodo-1H-pyrazol-1-yl)pyridine (75 mg), sodium carbonate (42 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (14 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-4-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine (29 mg). MS m/z (M+H): 308.

New learning discoveries about 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

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.

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)dichloropalladium(II) (366 mg), 1,4-dioxane (24 mL), and water (2.4 mL) was stirred at 110 C. for 5 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, water was added thereto, and the solid matter was collected by filtration. The obtained solid matter was suspended by the addition of ethyl acetate, and the solid matter was collected by filtration, thereby obtaining 2-chloro-7-(1H-pyrazol-4-yl)-1,5-naphthyridine (2.6 g) as a pale brown solid. MS m/z (M+H): 231., 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