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[ CAS No. 886365-43-1 ]

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Chemical Structure| 886365-43-1
Chemical Structure| 886365-43-1
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Product Details of [ 886365-43-1 ]

CAS No. :886365-43-1 MDL No. :MFCD07375125
Formula : C7H6BrNO2 Boiling Point : 330.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :216.03 g/mol Pubchem ID :45789779
Synonyms :

Safety of [ 886365-43-1 ]

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 [ 886365-43-1 ]

  • Upstream synthesis route of [ 886365-43-1 ]
  • Downstream synthetic route of [ 886365-43-1 ]

[ 886365-43-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 886365-43-1 ]
  • [ 74-88-4 ]
  • [ 213771-32-5 ]
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
  • 2
  • [ 886365-43-1 ]
  • [ 213771-32-5 ]
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
  • 3
  • [ 67-56-1 ]
  • [ 886365-43-1 ]
  • [ 213771-32-5 ]
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
  • 4
  • [ 156072-86-5 ]
  • [ 886365-43-1 ]
YieldReaction ConditionsOperation in experiment
98% With water; sodium hydroxide In ethanol at 80℃; for 1.5 h; Step B
5-bromo-3-methylpyridine-2-carboxylic acid
To a solution of 5-bromo-3-methylpyridine-2-carbonitrile (3.9 g, 20 mmol) in ethanol (30 mL) was added 6.0 M sodium hydroxide in water (15 mL), and the reaction was stirred at 80° C. for 1.5 h.
The reaction mixture was concentrated, diluted with water and partitioned in EtOAc.
The aqueous phase was acidified to pH 2-3.
The product then was extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered and concentrated to give 4.2 g (98percent yield) of the desired product as a yellow solid.
98%
Stage #1: at 80℃; for 1.5 h;
Stage #2: Acidic aqueous solution
Example 10.1: 5-bromo-3-methylpyridine-2-carboxylic acid; To a suspension of 5-bromo-3-methylpyridine-2-carbonitrile (1.22 g, 7.21 mmol) in ethanol (10 mL) was added 6N sodium hydroxide (5 mL) and the reaction was stirred at 80 <n="35"/>0C for 1.5 h. The organic was concentrated and the reaction mixture was dilute with water and partitioned in ethyl acetate. The aqueous phase was acidified to pH 2-3. The product was extracted with ethyl acetate, washed with brine, dried over sodium sulphate, filtered and concentrated to afford the product as a yellow solid (185 mg, 98percent). 5H NMR (300 MHz, CDCl3): δ 8.54 (bs, IH), 7.90 (s, IH), 2.76 (s, 3H).
Reference: [1] Patent: US2013/96144, 2013, A1, . Location in patent: Paragraph 0390; 0391
[2] Patent: WO2008/100715, 2008, A1, . Location in patent: Page/Page column 33-34
  • 5
  • [ 3430-18-0 ]
  • [ 886365-43-1 ]
Reference: [1] Patent: US2013/96144, 2013, A1,
[2] Patent: WO2008/100715, 2008, A1,
  • 6
  • [ 886365-43-1 ]
  • [ 1346809-61-7 ]
Reference: [1] Patent: WO2011/154677, 2011, A1,
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