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[ CAS No. 213771-32-5 ]

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Chemical Structure| 213771-32-5
Chemical Structure| 213771-32-5
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CAS No. :213771-32-5 MDL No. :MFCD07375126
Formula : C8H8BrNO2 Boiling Point : 302.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :230.06 g/mol Pubchem ID :45789787
Synonyms :

Safety of [ 213771-32-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 213771-32-5 ]

  • Upstream synthesis route of [ 213771-32-5 ]
  • Downstream synthetic route of [ 213771-32-5 ]

[ 213771-32-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 213771-32-5 ]
  • [ 794592-14-6 ]
Reference: [1] Patent: US2014/107109, 2014, A1,
[2] Patent: WO2016/22724, 2016, A1,
  • 2
  • [ 886365-43-1 ]
  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.666667 h; Step C
methyl 5-bromo-3-methylpyridine-2-carboxylate
To a solution 5-bromo-3-methylpyridine-2-carboxylic acid (2.6 g, 12 mmol) in N,N-dimethylformamide (20.0 mL) was added potassium carbonate (4.99 g, 36.1 mmol) and methyl iodide (1.50 mL, 24.1 mmol) and the reaction was stirred 80° C. for 40 min.
The reaction mixture was partitioned with EtOAc and water.
The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 2.3 g (83percent yield) of the desired product as a yellow solid.
82% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.666667 h; Example 11.1: methyl S-bromo-S-metliylpyridine-Z-carboxylateO; To a solution of 5-bromo-3-methylpyridine-2-carboxylic acid (450 mg, 2.08 mmol) in dimethylformamide (2 mL) was added potassium carbonate (862 mg, 6.24 mmol) and iodomethane (739 mg, 5.21 mmol) and the reaction was stirred at 80 0C for 40 min. The reaction mixture was partitioned with ethyl acetate and water and the organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated to afford the product as a yellow solid (380 mg, 82percent). 1H NMR (300 MHz, CDCl3): δ 8.91 (s, IH), 7.86 (s, IH), 3.98 (s, 3H), 2.60 (s, 3H).
Reference: [1] Patent: US2013/96144, 2013, A1, . Location in patent: Paragraph 0392; 0393
[2] Patent: WO2008/100715, 2008, A1, . Location in patent: Page/Page column 34
  • 3
  • [ 67-56-1 ]
  • [ 3430-18-0 ]
  • [ 201230-82-2 ]
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Reference: [1] Patent: EP977739, 2003, B1, . Location in patent: Page/Page column 9-10
  • 4
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YieldReaction ConditionsOperation in experiment
99% With thionyl chloride In methanol for 6 h; Reflux To a mixture of 5-bromo-3-methylpicolinic acid (600 mg, 2.8 mmol) in MeOH (10 mL) was added 50C12 (397 mg, 3.3 mmol). The mixture was stirred at reflux temperature for 6 hours. LCMS showed the reaction was complete. The reaction mixture was evaporated in vacuo to afford methyl 5-bromo-3-methylpicolinate (640 mg, 99percent yield), m/z = 229.76(M+H), as an off-white solid.
Reference: [1] Patent: WO2016/127074, 2016, A1, . Location in patent: Page/Page column 31; 32
  • 5
  • [ 67-56-1 ]
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Reference: [1] Patent: WO2011/154677, 2011, A1, . Location in patent: Page/Page column 91-92
[2] Patent: US2016/176882, 2016, A1, . Location in patent: Paragraph 0466; 0467
[3] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00245
  • 6
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Reference: [1] Patent: US2006/199817, 2006, A1, . Location in patent: Page/Page column 27
  • 7
  • [ 3430-18-0 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: US2013/96144, 2013, A1,
[2] Patent: WO2008/100715, 2008, A1,
  • 8
  • [ 156072-86-5 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: US2013/96144, 2013, A1,
[2] Patent: WO2008/100715, 2008, A1,
  • 9
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  • [ 1346809-61-7 ]
Reference: [1] Patent: WO2011/154677, 2011, A1,
Historical Records

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