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[ CAS No. 132873-77-9 ] {[proInfo.proName]}

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Chemical Structure| 132873-77-9
Chemical Structure| 132873-77-9
Structure of 132873-77-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 132873-77-9 ]

CAS No. :132873-77-9 MDL No. :MFCD13182538
Formula : C13H15BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RJQPRKXEVWZMAO-UHFFFAOYSA-N
M.W : 311.17 Pubchem ID :15744964
Synonyms :

Safety of [ 132873-77-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 132873-77-9 ]

* 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.

  • Upstream synthesis route of [ 132873-77-9 ]
  • Downstream synthetic route of [ 132873-77-9 ]

[ 132873-77-9 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1352721-36-8 ]
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YieldReaction ConditionsOperation in experiment
37% With phosphorus tribromide In diethyl ether; dichloromethane at 0 - 20℃; for 2.08333 h; Inert atmosphere Intermediate AG: 4-Bromomethyl-benzoimidazole-1-carboxylic acid tert-butyl esterTo a solution of 4-Hydroxymethyl-benzoimidazole-1 -carboxylic acid tert-butyl ester (Step AG1 , 330 mg, 1 .329 mmol) in Et20 (5 ml) at 0 °C under Ar was added PBr3 (1 M in CH2CI2) (1.462 ml, 1.462 mmol), dropwise, causing a thick precipitation. After 5 minutes at 0 °C, the medium was allowed to reach rt. After 1 h at rt, PBr3 (1 M in CH2CI2) (0.133 ml, 0.133 mmol) was added under stirring, followed by CH2CI2 (2 ml). After a further 1 h at rt, the medium was carefully quenched with saturated sodium bicarbonate solution (20 ml, strong C02 evolution) and extracted with EtOAc (3 x 15 ml). Drying of the combined organics over Na2S04 and concentration afforded a clear oil. The oil was purified by chromatography on silica gel, using a 0percent to 100percent gradient of eluent B (EtOAc/ CH2CI2 / heptane: 1/2/2) in eluent A (heptane/ CH2CI2 : 1/1 ), yielding the title product as a colorless oil, 153 mg (37percent). HPLC/MS (Method A) tR1.70 minute, M+H 310.9-312.9 . 1 H NMR (DMSO-d6) Ppm 1 .69 (s, 9 H) 4.95 (s, 2 H) 7.38 (m, 2 H) 7.94 (d, 1 H) 8.49 (s, 1 H).
37% With phosphorus tribromide; sodium hydrogencarbonate In diethyl ether; dichloromethane at 0 - 20℃; for 2.08333 h; Argon atmosphere Intermediate AG: 4-Bromomethyl-benzoimidazole-1-carboxylic acid tert-butyl esterTo a solution of 4-Hydroxymethyl-benzoimidazole-1 -carboxylic acid tert-butyl ester (Step AG1 , 330 mg, 1 .329 mmol) in Et20 (5 ml) at 0 °C under Ar was added PBr3 (1 M in CH2CI2) (1.462 ml, 1.462 mmol), dropwise, causing a thick precipitation. After 5 minutes at 0 °C, the medium was allowed to reach rt. After 1 h at rt, PBr3 (1 M in CH2CI2) (0.133 ml, 0.133 mmol) was added under stirring, followed by CH2CI2 (2 ml). After a further 1 h at rt, the medium was carefully quenched with saturated sodium bicarbonate solution (20 ml, strong C02 evolution) and extracted with EtOAc (3 x 15 ml). Drying of the combined organics over Na2S04 and concentration afforded a clear oil. The oil was purified by chromatography on silica gel, using a 0percent to 100percent gradient of eluent B (EtOAc/ CH2CI2 / heptane: 1/2/2) in eluent A (heptane/ CH2CI2 : 1/1 ), yielding the title product as a colorless oil, 153 mg (37percent). HPLC/MS (Method A) tR1.70 minute, M+H 310.9-312.9 . 1 H NMR (DMSO-d6) Ppm 1 .69 (s, 9 H) 4.95 (s, 2 H) 7.38 (m, 2 H) 7.94 (d, 1 H) 8.49 (s, 1 H).
Reference: [1] Patent: WO2011/157793, 2011, A1, . Location in patent: Page/Page column 47
[2] Patent: WO2011/157787, 2011, A1, . Location in patent: Page/Page column 70-71
  • 2
  • [ 139525-24-9 ]
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YieldReaction ConditionsOperation in experiment
42% With N-Bromosuccinimide In tetrachloromethane C.
4-(Bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester
A mixture of 4-methylbenzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (6.50 g, 28.0 mmol) and N-bromosuccinimide (5.50 g, 30.9 mmol) in carbon tetrachloride (75 mmol) was stirred and irradiated with a 250 W flood lamp for 1 h.
The reaction mixture was allowed to cool and the solid was filtered off and discarded.
The filtrate was evaporated and purified by HPLC (20percent ethyl acetate/hexanes) to give 4-(bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (3.69 g, 42percent).
Reference: [1] Patent: US6331640, 2001, B1,
  • 3
  • [ 139525-24-9 ]
  • [ 132875-27-5 ]
  • [ 132873-77-9 ]
Reference: [1] Patent: US5273975, 1993, A,
  • 4
  • [ 139525-24-9 ]
  • [ 132873-77-9 ]
  • [ 132875-27-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1076 - 1092
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1076 - 1092
  • 5
  • [ 24424-99-5 ]
  • [ 132873-77-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1076 - 1092
[2] Patent: WO2011/157787, 2011, A1,
  • 6
  • [ 4887-83-6 ]
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Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1076 - 1092
  • 7
  • [ 37619-25-3 ]
  • [ 132873-77-9 ]
Reference: [1] Patent: WO2011/157793, 2011, A1,
[2] Patent: WO2011/157787, 2011, A1,
  • 8
  • [ 65658-13-1 ]
  • [ 132873-77-9 ]
Reference: [1] Patent: WO2011/157787, 2011, A1,
  • 9
  • [ 24424-99-5 ]
  • [ 65658-13-1 ]
  • [ 132873-77-9 ]
Reference: [1] Patent: WO2011/157793, 2011, A1,
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