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Chemical Structure| 666734-80-1 Chemical Structure| 666734-80-1

Structure of 666734-80-1

Chemical Structure| 666734-80-1

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Product Details of [ 666734-80-1 ]

CAS No. :666734-80-1
Formula : C12H12N2O2
M.W : 216.24
SMILES Code : OC1=CC(C)=C(C)N=C1C2=NC=CC=C2O

Safety of [ 666734-80-1 ]

Application In Synthesis of [ 666734-80-1 ]

* 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 [ 666734-80-1 ]

[ 666734-80-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 68500-37-8 ]
  • [ 666734-80-1 ]
  • 3-(7-Methoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dmap; caesium carbonate; In dimethyl sulfoxide; at 130℃; 4-Chloro-7-methoxyquinoline (170 mg), 5,6-dimethyl-[2,2']bipyridinyl-3-ol (176 mg), and 4-dimethylaminopyridine (322 mg) were dissolved in dimethylsulfoxide (2 ml). Cesium carbonate (860 mg) was added to the solution, and the mixture was stirred at 130°C overnight. The mixture was cooled to room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (273 mg, yield 87percent). 1H-NMR (CDCl3, 400 MHz): delta 2.39 (s, 3H), 2.66 (s, 3H), 3.96 (d, J = 1.2 Hz, 3H), 6.34 (dd, J = 2.2, 5.4 Hz, 1H), 7.10 (m, 1H), 7.21 (m, 1H), 7.36 (s, 1H), 7.40 (m, 1H), 7.57 (m, 1H), 7.81 (dd, J = 1.2, 8.1 Hz, 1H), 8.23 (dd, J = 1.5, 9.3 Hz, 1H), 8.48 - 8.49 (m, 2H) Mass spectrometric value (ESI-MS, m/z): 380 (M+Na)+
  • 2
  • [ 666734-80-1 ]
  • [ 13790-39-1 ]
  • 4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-6,7-dimethoxy-quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With caesium carbonate; In dimethyl sulfoxide; at 120℃; Dimethylsulfoxide (2.5 ml) was added to 5,6-dimethyl-[2,2']bipyridinyl-3-ol (50 mg), <strong>[13790-39-1]4-chloro-6,7-dimethoxyquinazoline</strong> (169 mg), and cesium carbonate (244 mg), and the mixture was stirred at 120C overnight. The reaction mixture was cooled to room temperature, water was added to the cooled mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with an ethyl acetate system to give the title compound (79 mg, yield 81%). 1H-NMR (CDCl3, 400 MHz): δ 2.41 (s, 3H), 2.63 (s, 3H), 4.03 (s, 3H), 4.05 (s, 3H), 7.06 (ddd, 7.6, 4.9, 1.2 Hz, 1H), 7.28 (s, 1H), 7.50 (s, 1H), 7.55 (s, 1H), 7.62 (ddd, J = 7.6, 4.9, 1.7 Hz, 1H), 7.89 (d, J = 7.8 Hz, 1H), 8.26 (d, J = 4.1 Hz, 1H), 8.48 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 411 (M+Na)+
  • 3
  • [ 249889-68-7 ]
  • [ 666734-80-1 ]
  • 8-(5,6-Dimethyl-[2,2']bipyridinyl-3-yloxy)-2-methoxy-[1,5]naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dmap; caesium carbonate; In dimethyl sulfoxide; at 130℃; The residue was suspended in diisopropylethylamine (7 ml), phosphorus oxychloride (1.5 ml) was added to the suspension, and the mixture was stirred at 100C for one hr. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give <strong>[249889-68-7]8-chloro-2-methoxy-[1,5]naphthyridine</strong> (572 mg, yield 29%) (3 steps). 8-Chloro-2-methoxy-[1,5]naphthyridine (50 mg), 5,6-dimethyl-[2,2']bipyridinyl-3-ol (51 mg), and 4-dimethylaminopyridine (94 mg) were dissolved in dimethylsulfoxide (1.5 ml), cesium carbonate (251 mg) was added to the solution, and the mixture was stirred at 130C overnight. The reaction mixture was cooled to room temperature, and water was added thereto. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (70 mg, yield 75%). 1H-NMR (CDCl3, 400 MHz): delta 2.34 (s, 3H), 2.66 (s, 3H), 3.92 (s, 3H), 6.92 (d, J = 5.4 Hz, 1H), 7.17 - 7.26 (m, 3H), 7.65 (dd, J = 7.6, 7.6 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 8.36 (s, 1H), 8.53 (d, J = 5.9 Hz, 1H), 8.58 (m, 1H) Mass spectrometric value (ESI-MS, m/z): 381 (M+Na)+
  • 4
  • [ 417721-36-9 ]
  • [ 666734-80-1 ]
  • 4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-7-methoxy-quinoline-6-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With dmap; caesium carbonate; In dimethyl sulfoxide; at 130℃; Methyl 4-chloro-7-methoxy-quinoline-6-carboxylate (120 mg) was dissolved in methanol (6 ml), 28percent aqueous ammonia (6 ml) was added thereto, and the mixture was stirred at 40°C overnight. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give 4-chloro-7-methoxy-quinoline-6-carboxylic acid amide (91 mg, yield 80percent). 4-Chloro-7-methoxy-quinoline-6-carboxylic acid amide (91 mg), 5,6-dimethyl-[2,2']bipyridinyl-3-ol (115 mg), and 4-dimethylaminopyridine (141 mg) were dissolved in dimethylsulfoxide (3 ml), cesium carbonate (375 mg) was added to the solution, and the mixture was stirred overnight at 130°C. The mixture was cooled to room temperature, and water was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (33 mg, yield 22percent). 1H-NMR (CDCl3, 400 MHz): delta 2.40 (s, 3H), 2.67 (s, 3H), 4.13 (s, 3H), 5.92 (m, 1H), 6.39 (d, J = 5.4 Hz, 1H), 7.08 (ddd, J = 1.2, 4.9, 7.6 Hz, 1H), 7.36 (s, 1H), 7.56 - 7.63 (m, 2H), 7.76 (m, 1H), 7.90 (m, 1H), 8.40 (m, 1H), 8.54 (d, J = 5.6 Hz, 1H), 9.27 (d, J = 1.0 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 423 (M+Na)+
  • 5
  • [ 666734-80-1 ]
  • [ 25759-94-8 ]
  • 3-(7-Fluoro-6-methoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With dmap; caesium carbonate; In dimethyl sulfoxide; at 130℃; 4-Chloro-7-fluoro-6-methoxy-quinoline (50 mg), 5,6-dimethyl-[2,2']bipyridinyl-3-ol (47 mg), and 4-dimethylaminopyridine (87 mg) were dissolved in dimethylsulfoxide (1.5 ml), cesium carbonate (231 mg) was added to the solution, and the mixture was stirred at 130C overnight. The reaction mixture was cooled to room temperature, and water was added thereto. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (47 mg, yield 52%). 1H-NMR (CDCl3, 400 MHz): δ 2.41 (s, 3H), 2.67 (s, 3H), 4.04 (s, 3H), 6.47 (d, J = 5.6 Hz, 1H), 7.11 (ddd, J = 1.0, 4.9, 7.6 Hz, 1H), 7.39 (s, 1H), 7.63 (m, 1H), 7.70 (d, J = 9.0 Hz, 1H), 7.88 - 7.90 (m, 2H), 8.35 (m, 1H), 8.45 (d, J = 5.6 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 398 (M+Na)+
 

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