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Chemical Structure| 1309774-04-6

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Product Details of [ 1309774-04-6 ]

CAS No. :1309774-04-6
Formula : C8H6BrN3
M.W : 224.06
SMILES Code : NC1=NC2=CC(Br)=CN=C2C=C1
MDL No. :MFCD29089336
InChI Key :WONDVTGZCODVDX-UHFFFAOYSA-N
Pubchem ID :58310532

Safety of [ 1309774-04-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1309774-04-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1309774-04-6 ]

[ 1309774-04-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1309774-03-5 ]
  • [ 1309774-04-6 ]
YieldReaction ConditionsOperation in experiment
85% With ammonium hydroxide; In 1,4-dioxane; at 140℃; for 24h;Sealed tube; In a sealed tube, a mixture of <strong>[1309774-03-5]7-bromo-2-chloro-1,5-naphthyridine</strong> 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]+.
80% With ammonia; In 1,4-dioxane; water; at 160℃; for 24h;Sealed reactor; Example 3.1 : 7-Bromo-[1 ,5]naphthyridin-2-ylamineIn a sealed reactor, 500 mg (1 .23 mmol, 1 eq) of 7-bromo-2-chloro-1 ,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2S04, 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 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C.1H-NMR (DMSO-d6, 400 MHz): delta = 8,57 (d, 1 H); 8,05 (d, 1 H); 7,96 (d, 1 H); 6,04 (d, 1 H); 6,98 (s, 2H) ppm.MS: m/z 225 (M+H+).
80% With ammonia; In 1,4-dioxane; water; at 160℃; for 24h;Sealed reactor; Example 3.1: 7-Bromo-[1,5]naphthyridin-2-ylamine [Show Image] In a sealed reactor, 500 mg (1.23 mmol, 1 eq) of <strong>[1309774-03-5]7-bromo-2-chloro-1,5-naphthyridine</strong> and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were 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 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C. 1H-NMR (DMSO-d6, 400 MHz): delta.= 8,57 (d, 1H); 8,05 (d, 1H); 7,96 (d, 1H); 6,04 (d, 1H); 6,98 (s, 2H) ppm. MS: m/z 225 (M+H+).
90 mg With ammonium hydroxide; In 1,4-dioxane; water; at 120℃; for 3h;Microwave irradiation; A mixed solution of the compound 0001-3 (100 mg) in 1,4-dioxane (2 ml) and a 25% aqueous ammonia solution was stirred at 120C for 3 hours using a microwave reaction device. The reaction solution was cooled, and brine and ethyl acetate were added thereto. The organic layer was separated and then dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain a 0001-4 (90 mg) as a white solid. 1H-NMR (DMSO-d6) delta: 8.53 (1H, d), 8.02 (1H, d), 7.92 (1H, d), 7.01 (1H, d), 6.94 (1H, s). MS m/z (M+H): 224,226.
90 mg With ammonium hydroxide; In 1,4-dioxane; at 120℃; for 3h;Microwave irradiation; 0031-1 A mixture solution of <strong>[1309774-03-5]7-bromo-2-chloro-1,5-naphthyridine</strong> (100 mg) in 1,4-dioxane (2 mL) and a 25% ammonia aqueous solution was stirred at 120 C. for 3 hours using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and a saturated sodium chloride aqueous solution and ethyl acetate were added thereto. The organic layer was collected by separation, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 7-bromo-1,5-naphthyridine-2-amine (90 mg) as a white solid. 1H-NMR (DMSO-d6) delta: 8.53 (1H, d), 8.0 (1H, d), 7.9 (1H, d), 7.0 (1H, d), 6.9 (1H, s). MS m/z (M+H): 224, 226.

 

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