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[ CAS No. 137178-88-2 ] {[proInfo.proName]}

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Chemical Structure| 137178-88-2
Chemical Structure| 137178-88-2
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Product Details of [ 137178-88-2 ]

CAS No. :137178-88-2 MDL No. :MFCD07368290
Formula : C6H3BrClNO Boiling Point : -
Linear Structure Formula :- InChI Key :IJJINPZOASSMGD-UHFFFAOYSA-N
M.W : 220.45 Pubchem ID :19090771
Synonyms :

Safety of [ 137178-88-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 137178-88-2 ]

* 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 [ 137178-88-2 ]
  • Downstream synthetic route of [ 137178-88-2 ]

[ 137178-88-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 137178-88-2 ]
  • [ 67-56-1 ]
  • [ 29682-15-3 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 45, p. 10748 - 10756
  • 2
  • [ 137178-88-2 ]
  • [ 64-17-5 ]
  • [ 77199-09-8 ]
Reference: [1] Patent: US2010/41642, 2010, A1, . Location in patent: Page/Page column 25
  • 3
  • [ 30766-11-1 ]
  • [ 137178-88-2 ]
YieldReaction ConditionsOperation in experiment
100% With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2 h; Oxalyl chloride (0.24 mmol) and 5 drops of N, N-dimethylformamide was added dropwise at room temperature, mixed with 5-bromo-pyrazolPiperidine carboxylic acid (0.05 mmol) in methylene chloride (80 ml). Was stirred at room temperature for 2 hours, the solvent was removed by distillation under reduced pressure to giveChloride 5.4 g (100percent).
99% at 80℃; for 2 h; Thionyl chloride (10 ml, 137 mmol) was added to 5-bromopicolinic acid (5.00 g, 24.75 mmol). A drop of DMF was added, and the mixture was heated at 80 °C for 2 h. The excess thionyl chloride was removed to afford 5-bromopicolinoyl chloride (5.413 g, 24.55 mmol, 99 percent yield) as a pale yellow solid. An aliquot was quenched with methanol to afford methyl 5-bromopicolinate. MS (ESI, pos. ion) m/z: 216, 218 (M + 1).
93% for 2 h; Inert atmosphere; Reflux Thionyl chloride (10 mL, 150 mmol) was added to solid 5-bromopicolinic acid (1 .2 g, 6 mmol) at ambient temperature under N2. The resulting mixture was refluxed for 2 h and the volatiles were removed in vacuo. The crude acid chloride was dissolved in dry DCM (20 mL) and the solution was slowly added at 0 °C to a solution of 2-amino-2-methylpropan-1-01 (1.6 g, 18 mmol) in DCM (5 mL). After stirring 48 h at ambient temperature, solvents were removed in vacuo and the crude product was purified by flash chromatography on silica gel (PEIEA= 100/1 to 5/1) to the title compound (1.5 g, 93 percent) as a white solid. LCMS: [M+H] = 273.1.
Reference: [1] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0533
[2] Patent: WO2014/164749, 2014, A1, . Location in patent: Page/Page column 312
[3] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00262
[4] Tetrahedron, 2005, vol. 61, # 45, p. 10748 - 10756
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 2074 - 2079
[6] Patent: WO2007/7041, 2007, A1, . Location in patent: Page/Page column 220-221
[7] Patent: WO2007/78251, 2007, A1, . Location in patent: Page/Page column 48-49
[8] Patent: WO2008/729, 2008, A1, . Location in patent: Page/Page column 75
[9] Patent: WO2008/2244, 2008, A2, . Location in patent: Page/Page column 34
[10] Patent: WO2007/147874, 2007, A1, . Location in patent: Page/Page column 130-131
[11] Journal of Medicinal Chemistry, 2009, vol. 52, # 18, p. 5685 - 5702
[12] Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6257 - 6269
[13] Patent: US2010/41642, 2010, A1, . Location in patent: Page/Page column 24
[14] Patent: US2007/129345, 2007, A1, . Location in patent: Page/Page column 33
[15] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 18, p. 5548 - 5551
[16] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3805 - 3808
[17] Transition Metal Chemistry, 2011, vol. 36, # 4, p. 403 - 407
[18] Angewandte Chemie - International Edition, 2012, vol. 51, # 27, p. 6672 - 6675
[19] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9589 - 9606
[20] Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 1038 - 1046
[21] Organic Letters, 2014, vol. 16, # 11, p. 3142 - 3145
[22] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3228 - 3236
[23] Patent: US2015/307465, 2015, A1, . Location in patent: Paragraph 0566
[24] Patent: US2016/176882, 2016, A1, . Location in patent: Paragraph 0494; 0495
[25] Patent: JP2016/11257, 2016, A, . Location in patent: Paragraph 0125-0127
[26] Angewandte Chemie - International Edition, 2016, vol. 55, # 39, p. 11897 - 11901[27] Angew. Chem., 2016, vol. 128, # 39, p. 12076 - 12080,5
[28] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1098 - 1117
[29] Patent: EP3279183, 2018, A1, . Location in patent: Paragraph 0485
  • 4
  • [ 29682-15-3 ]
  • [ 137178-88-2 ]
Reference: [1] Patent: WO2004/814, 2003, A1, . Location in patent: Page 69
  • 5
  • [ 97483-77-7 ]
  • [ 137178-88-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 2074 - 2079
  • 6
  • [ 624-28-2 ]
  • [ 137178-88-2 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 45, p. 10748 - 10756
  • 7
  • [ 3430-13-5 ]
  • [ 137178-88-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3228 - 3236
  • 8
  • [ 137178-88-2 ]
  • [ 1201644-47-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3805 - 3808
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