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[ CAS No. 14001-66-2 ]

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2D
Chemical Structure| 14001-66-2
Chemical Structure| 14001-66-2
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Product Details of [ 14001-66-2 ]

CAS No. :14001-66-2MDL No. :MFCD04973351
Formula : C5H5BrN2O Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :189.01Pubchem ID :139657
Synonyms :

Computed Properties of [ 14001-66-2 ]

TPSA : 35 H-Bond Acceptor Count : 3
XLogP3 : 1.2 H-Bond Donor Count : 0
SP3 : 0.20 Rotatable Bond Count : 1

Safety of [ 14001-66-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280UN#:N/A
Hazard Statements:H302-H317Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14001-66-2 ]

  • Upstream synthesis route of [ 14001-66-2 ]
  • Downstream synthetic route of [ 14001-66-2 ]

[ 14001-66-2 ] Synthesis Path-Upstream   1~11

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YieldReaction ConditionsOperation in experiment
60% at 70℃; Synthesis of Compound 11-3 (0400) To a solution of 11-2 (2.0 g, 10 mmol) in methanol (15 mL) was added CH3ONa (2.16 g, 40 mmol). The resulting mixture was stirred at 70° C. overnight. Methanol was evaporated in vacuum. Water (10 mL) was added carefully to the residue and the mixture was extracted with ethyl acetate (300 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford 11-3 as a yellow solid (1.17 g, 60percent).
1.17 g at 70℃; To a solution of 24-2 (2.0 g, 10 mmol) in methanol (15 ml) was added CH3ONa (2.16 g, 40 mmol). The resulting mixture was stirred at 70 °C overnight. Methanol was evaporated in vacuum. Water (10 ml) was added carefully to the residue and the mixture was extracted with ethyl acetate (300 ml x 3). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford 24-3 as a yellow solid (1.17 g, 60percent yield).
Reference: [1] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 289-290
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5849 - 5853
  • 2
  • [ 67-56-1 ]
  • [ 38353-06-9 ]
  • [ 14001-66-2 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 20, p. 4478 - 4481
  • 3
  • [ 67-56-1 ]
  • [ 32779-37-6 ]
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
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  • [ 67-56-1 ]
  • [ 32779-36-5 ]
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Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 77 - 105
[2] Patent: WO2012/177603, 2012, A2, . Location in patent: Page/Page column 74
  • 5
  • [ 14001-67-3 ]
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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 7, p. 455 - 461
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  • [ 67-56-1 ]
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Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 7, p. 455 - 461
  • 7
  • [ 14001-66-2 ]
  • [ 101803-06-9 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10480 - 10483
  • 8
  • [ 14001-66-2 ]
  • [ 628692-15-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 6, p. 852 - 857
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 77 - 105
  • 9
  • [ 121-43-7 ]
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  • [ 628692-15-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3630 - 3633
  • 10
  • [ 73183-34-3 ]
  • [ 14001-66-2 ]
  • [ 1052686-60-8 ]
YieldReaction ConditionsOperation in experiment
98% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,2-dimethoxyethane; ethanol; water; toluene at 85℃; Inert atmosphere To a solution of 24-3 (800 mg, 4.26 mmol) and potassium acetate (1.25 g, 12.77 mmol) in solvent (DME/H2.O/Tolunen/EtOH =10/1/6/3, 7 ml) was added Pd(dppf)Cl2.DCM (700 mg, 0.85 mmol) and Bis(pinacolato)diboron (2.44 g, 9.6 mmol). After having been degassed and recharged with nitrogen, the reaction mixture was stirred at 85 °C overnight. TLC showed the reaction was complete. After cooling to room temperature, water (10 ml) was added and extracted with ethyl acetate (30 ml x 3). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA = 5:1) to afford 24-4 as a yellow solid (1.0 g, 98percent yield).
98% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,2-dimethoxyethane; ethanol; water; toluene at 85℃; Inert atmosphere Synthesis of Compound 11-4 (0401) To a solution of 11-3 (800 mg, 4.26 mmol) and potassium acetate (1.25 g, 12.77 mmol) in solvent (DME/H2O/Toluenen/EtOH=10/1/6/3, 7 mL) was added Pd(dppf)Cl2.DCM (700 mg, 0.85 mmol) and Bis(pinacolato)diboron (2.44 g, 9.6 mmol). After having been degassed and recharged with nitrogen, the reaction mixture was stirred at 85° C. overnight. TLC showed the reaction was complete. After cooling to room temperature, water (10 mL) was added and extracted with ethyl acetate (30 mL×3). The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=5:1) to afford 11-4 as a yellow solid (1.0 g, 98percent).
90% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; 1,2-dimethoxyethane at 150℃; for 0.25 h; Inert atmosphere; Microwave irradiation A mixture of 5-bromo-2-methoxypyrimidine (0.903 g, 4.78 mmol), 4,4,4',4',5,5,5',5'- octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.46 g, 5.74 mmol), PdCl2dppf(DCM) (0.114 g, 0.14 mmol) and KOAc (1.407 g, 14.34 mmol) were placed under Ar in a 20 mL microwave flask. Anhydrous 1,2-dimethoxyethane (16 mL) was added and the flask was irradiated at 150 oC for 15 minutes. Note starting material and product are indistinguishable by TLC. The material was concentrated and slurried in EtOAc. The material was then filtered through celite and purified by column chromatography 0 to 60 percent EtOAC in Hexanes. The compound was isolated as a white solid (1.01 g, 90 percent yield).1H NMR (400 MHz, CDCl3) δ 8.97 (s, 2H), 4.20 (s, 3H), 1.50 (s, 12H).13C NMR (100 MHz, CDCl3) δ 165.7, 84.5, 77.4, 55.1, 25.2, 25.0. HRMS (EI+) m/z calculated for C11H17BN2O3 [M+H]+: 237.1405, found: 237.14008.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5849 - 5853
[2] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 290
[3] Patent: WO2017/197151, 2017, A1, . Location in patent: Page/Page column 40
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  • [ 185990-03-8 ]
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Reference: [1] Chemical Science, 2015, vol. 6, # 5, p. 2943 - 2951
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