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[ CAS No. 1388056-45-8 ] {[proInfo.proName]}

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Chemical Structure| 1388056-45-8
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Product Details of [ 1388056-45-8 ]

CAS No. :1388056-45-8 MDL No. :MFCD29043506
Formula : C10H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 242.12 Pubchem ID :-
Synonyms :

Safety of [ 1388056-45-8 ]

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Precautionary Statements: UN#:
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Application In Synthesis of [ 1388056-45-8 ]

* 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 [ 1388056-45-8 ]

[ 1388056-45-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 938-33-0 ]
  • [ 1388056-45-8 ]
Reference： [1]Patent: WO2012/122716,2012,A1
  • 2
  • [ 53899-17-5 ]
  • [ 1388056-45-8 ]
YieldReaction ConditionsOperation in experiment
79% With N-Bromosuccinimide In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 1h; 19.C Step C - Synthesis of Comp; To a solution of compound Int-19b (17 g, 0.104 mol) in THF / D F (200 mL / 100 mL) at -30 °C was added NBS (20 g, 0.1 15 mol) in portions and the mixture was allowed to stir at -30 °C for 1 hour. The mixture was diluted with water and EtOAc and the water layer was extracted with EtOAc. The organic extract was washed with brine, dried over a2S0 , filtered and concentrated in vacuo to provide a residue which was purified using flash chromatography on silica gel (petroleum ether :EtOAc = 10.1 ) to provide compound Int-19c as yellow oil (20g, 79%).
79% With N-Bromosuccinimide In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 1h; 19.C Step C - Synthesis of Compound Int-19cInt 19b Int 19c To a solution of compound Int-19b (17 g, 0.104 mol) in THF / DMF (200 mL / 100 mL) at -30 °C was added BS (20 g, 0.115 mol) in portions and the mixture was allowed to stir at -30 °C for 1 hour. The mixture was diluted with water and EtOAc and the water layer was extracted with EtOAc. The organic extract was washed with brine, dried over Na2S04, filtered and concentrated in vacuo to provide a residue which was purified using flash chromatography on silica gel (petroleum ether :EtOAc = 10: 1) to provide compound Int-19c as yellow oil (20g, 79%).
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2012/125926, 2012, A2 Location in patent: Page/Page column 69-70
[2]Current Patent Assignee: MERCK & CO INC - WO2012/122716, 2012, A1 Location in patent: Page/Page column 88-89
  • 3
  • [ 635-46-1 ]
  • [ 475159-35-4 ]
  • [ 1388056-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine / chloroform / 2 h / 20 °C 2: copper(l) iodide; sodium / N,N-dimethyl-formamide / 20 h / 150 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: bromine / chloroform / 2 h / 20 °C 2: copper(l) iodide; sodium / N,N-dimethyl-formamide / 48 h / 150 °C / Inert atmosphere
Reference： [1]Oekten, Salih; Cakmak, Osman; Erenler, Ramazan; Yuece, Oenem; Tekin, Saban [Turkish Journal of Chemistry, 2013, vol. 37, # 6, p. 896 - 908]
[2]Oekten, Salih; Cakmak, Osman; Erenler, Ramazan; Yuece, Oenem; Tekin, Saban [Turkish Journal of Chemistry, 2013, vol. 37, # 6, p. 896 - 908]
  • 4
  • [ 67-56-1 ]
  • [ 190843-73-3 ]
  • [ 475159-35-4 ]
  • [ 1388056-45-8 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; sodium In N,N-dimethyl-formamide at 150℃; for 20h; Inert atmosphere; 4.2. Synthesis of the methoxy derivatives of 1,2,3,4-tetrahydroquinoline Freshly cut Na (1.5 g, 65.2 mmol) was added to dry MeOH (40 mL) under an Ar atmosphere. After completedissolution, the warm solution was diluted with dry DMF, and vacuum-dried CuI (1.78 g, 3.44 mmol) wasadded. Next, 6,8-dibromo-1,2,3,4-tetrahyroquinoline (2) (1 g, 3.44 mmol) in dry DMF (25 mL) was added tothe mixture, which was stirred magnetically under an Ar atmosphere at reux (ca. 150 C) for 48 h. The reaction progress was monitored by TLC. After cooling to rt, H2O (50 mL) was added to the mixture, and theaq layer was extracted with CHCl3 (3 50 mL). The organic layers were combined, washed with H2O (3 25mL), and dried (Na2SO4) . After ltration and removing the solvent, the residue was ltered through a shortsilica gel column (5.0 g). A mixture (400 mg) of 8-bromo-6-methoxyquinoline (3), 6-bromo-8-methoxyquinoline(4), and 6,8-dimethoxyquinoline (5) was obtained in a ratio of 15:50:35, respectively, as assigned by 1H NMR.The mixture was puried by silica gel (SiO2 , 60 g) column chromatography, eluting with AcOEt/hexane, (600mL, 1:9). Compounds 5 and 6 were collected as a mixture in the rst eluent (320 mL). However, after thesolvent polarity was increased to 2:9 AcOEt/hexane, compound 4 (112 mg, 14%) was isolated in pure form(second eluent 150 mL). After the solvent polarity was increased to 3:9 (AcOEt/hexane), the third eluent (100mL) was a mixture of products 4 and 5. Lastly, 6,8-dimethoxide 5 (120 mg, 18%) was isolated as a puresubstance, as the fourth eluent (240 mL). The reaction was repeated for 20 (entry 1) and 120 h (entry 3) underthe same reaction conditions. In the 20-h reaction, the product ratio of 6-bromo-8-methoxide 4 and 8-bromo-6-methoxide 3 was 50:50, respectively. In the 120-h reaction, 6-bromo-8-methoxide 4 and 6,8-dimethoxide 5were isolated in a ratio of 25:75, respectively (entry 3). The reactions were also repeated for 144 h and 192 husing the same reaction conditions. The ratios of the products are shown in Scheme 1 (entries 4 and 5). Thereaction was also repeated under the same reaction conditions with CuI but not MeONa for 3 days. However,no conversion (aromatization) was observed.
Reference： [1]Oekten, Salih; Cakmak, Osman; Erenler, Ramazan; Yuece, Oenem; Tekin, Saban [Turkish Journal of Chemistry, 2013, vol. 37, # 6, p. 896 - 908]
  • 5
  • [ 67-56-1 ]
  • [ 190843-73-3 ]
  • [ 475159-35-4 ]
  • [ 1388056-45-8 ]
  • 6,8-dimethoxy-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 18% 2: 14% With copper(l) iodide; sodium In N,N-dimethyl-formamide at 150℃; for 48h; Inert atmosphere; 4.2. Synthesis of the methoxy derivatives of 1,2,3,4-tetrahydroquinoline Freshly cut Na (1.5 g, 65.2 mmol) was added to dry MeOH (40 mL) under an Ar atmosphere. After completedissolution, the warm solution was diluted with dry DMF, and vacuum-dried CuI (1.78 g, 3.44 mmol) wasadded. Next, 6,8-dibromo-1,2,3,4-tetrahyroquinoline (2) (1 g, 3.44 mmol) in dry DMF (25 mL) was added tothe mixture, which was stirred magnetically under an Ar atmosphere at reux (ca. 150 C) for 48 h. The reaction progress was monitored by TLC. After cooling to rt, H2O (50 mL) was added to the mixture, and theaq layer was extracted with CHCl3 (3 50 mL). The organic layers were combined, washed with H2O (3 25mL), and dried (Na2SO4) . After ltration and removing the solvent, the residue was ltered through a shortsilica gel column (5.0 g). A mixture (400 mg) of 8-bromo-6-methoxyquinoline (3), 6-bromo-8-methoxyquinoline(4), and 6,8-dimethoxyquinoline (5) was obtained in a ratio of 15:50:35, respectively, as assigned by 1H NMR.The mixture was puried by silica gel (SiO2 , 60 g) column chromatography, eluting with AcOEt/hexane, (600mL, 1:9). Compounds 5 and 6 were collected as a mixture in the rst eluent (320 mL). However, after thesolvent polarity was increased to 2:9 AcOEt/hexane, compound 4 (112 mg, 14%) was isolated in pure form(second eluent 150 mL). After the solvent polarity was increased to 3:9 (AcOEt/hexane), the third eluent (100mL) was a mixture of products 4 and 5. Lastly, 6,8-dimethoxide 5 (120 mg, 18%) was isolated as a puresubstance, as the fourth eluent (240 mL). The reaction was repeated for 20 (entry 1) and 120 h (entry 3) underthe same reaction conditions. In the 20-h reaction, the product ratio of 6-bromo-8-methoxide 4 and 8-bromo-6-methoxide 3 was 50:50, respectively. In the 120-h reaction, 6-bromo-8-methoxide 4 and 6,8-dimethoxide 5were isolated in a ratio of 25:75, respectively (entry 3). The reactions were also repeated for 144 h and 192 husing the same reaction conditions. The ratios of the products are shown in Scheme 1 (entries 4 and 5). Thereaction was also repeated under the same reaction conditions with CuI but not MeONa for 3 days. However,no conversion (aromatization) was observed.
Reference： [1]Oekten, Salih; Cakmak, Osman; Erenler, Ramazan; Yuece, Oenem; Tekin, Saban [Turkish Journal of Chemistry, 2013, vol. 37, # 6, p. 896 - 908]

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