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[ CAS No. 29682-15-3 ]

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2D
Chemical Structure| 29682-15-3
Chemical Structure| 29682-15-3
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Product Details of [ 29682-15-3 ]

CAS No. :29682-15-3MDL No. :MFCD04112493
Formula : C7H6BrNO2 Boiling Point : 290.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :216.03Pubchem ID :7016458
Synonyms :

Computed Properties of [ 29682-15-3 ]

TPSA : 39.2 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.14 Rotatable Bond Count : 2

Safety of [ 29682-15-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29682-15-3 ]

  • Upstream synthesis route of [ 29682-15-3 ]
  • Downstream synthetic route of [ 29682-15-3 ]

[ 29682-15-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 29682-15-3 ]
  • [ 107504-07-4 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3792 - 3795
  • 2
  • [ 29682-15-3 ]
  • [ 168823-76-5 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 38, p. 10670 - 10681
  • 3
  • [ 29682-15-3 ]
  • [ 137178-88-2 ]
Reference: [1] Patent: WO2004/814, 2003, A1, . Location in patent: Page 69
  • 4
  • [ 29682-15-3 ]
  • [ 1158763-55-3 ]
Reference: [1] Patent: WO2012/3189, 2012, A1,
  • 5
  • [ 29682-15-3 ]
  • [ 1201326-81-9 ]
Reference: [1] Patent: WO2012/76898, 2012, A1,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3012 - 3023
  • 6
  • [ 29682-15-3 ]
  • [ 1380672-71-8 ]
Reference: [1] Patent: WO2012/76898, 2012, A1,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3012 - 3023
  • 7
  • [ 29682-15-3 ]
  • [ 1380672-07-0 ]
Reference: [1] Patent: WO2012/76898, 2012, A1,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3012 - 3023
  • 8
  • [ 29682-15-3 ]
  • [ 1214353-79-3 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 60℃; for 20 h;
Stage #2: at 0 - 95℃; for 2 h;
A mixture of 5-bromo-pyridine-2-carboxylic acid methyl ester (CAN 29682-15-3, 50 g, 0.23 mol) and m-CPBA (CAN 937-14-4, 80 g, 0.46 mol) in 400 mL dry methylene chloride was heated to 60° C. for 20 h. After that, the mixture was quenched with saturated sodium sulfite solution and extracted with ethyl acetate (2.x.200 mL). The organic layer was washed with brine (2.x.200 mL) and evaporated to dryness. The residue was purified by column chromatography (silica gel, 300 g, eluting with 15percent ethyl acetate in petroleum ether) to obtain a brown oil. The brown oil, 5-bromo-2-(methoxycarbonyl)pyridine 1-oxide (30 g, 0.13 mol) was added into phosphoryl trichloride (CAN 10025-87-3, 80 mL) at 0° C. over 1 h, then the mixture was heated to 95° C. for 1 h. After that the mixture was evaporated to dryness, the residue was dissolved in water (50 mL), extracted with ethyl acetate (3.x.50 mL) and the organic layer was evaporated to dryness to obtain the product as a white solid (19 g, 59percent); MS (EI): m/e=249.9 [M+H]+.
Reference: [1] Patent: US2012/316147, 2012, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2012/168350, 2012, A1,
[3] Patent: WO2014/86806, 2014, A1,
[4] Patent: WO2014/86705, 2014, A1,
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4266 - 4277
[6] Patent: WO2016/44662, 2016, A1,
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