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[ CAS No. 886365-25-9 ]

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Chemical Structure| 886365-25-9
Chemical Structure| 886365-25-9
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CAS No. :886365-25-9 MDL No. :MFCD07375112
Formula : C8H8BrNO3 Boiling Point : 276.4±35.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :246.06 g/mol Pubchem ID :46311225
Synonyms :

Safety of [ 886365-25-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886365-25-9 ]

  • Upstream synthesis route of [ 886365-25-9 ]
  • Downstream synthetic route of [ 886365-25-9 ]

[ 886365-25-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 886365-25-9 ]
  • [ 913836-17-6 ]
Reference: [1] Patent: US2014/94456, 2014, A1,
[2] Patent: WO2015/153683, 2015, A1,
  • 2
  • [ 886365-25-9 ]
  • [ 886365-22-6 ]
YieldReaction ConditionsOperation in experiment
62% With lithium hydroxide monohydrate; water In tetrahydrofuran at 25℃; for 2 h; A mixture of lithium hydroxide monohydrate (13.98g, 333.25mmol) and methyl 5- bromo-2-methoxy-pyridine-4-carboxylate (16 .40g, 66 .65mmol) in tetrahydrofuran (30mL) /water (6mL) was stirred at 25 °C for 2 h. The mixture was concentrated under reduced pressure. The aqueous residue was diluted with water (l0mL) and adjusted to pH=4 by addition of hydrochloric acid (2 M, 80 mL). The mixture was extracted with ethyl acetate (3 x 1 0mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford crude 5-bromo-2-methoxy-pyridine-4-carboxylic acid (9.62g,62percent) as brown oil. LCMS RT = 0.448 mi m/z = 231.9 [M + H]. LCMS (5 to 95percent acetonitrile in water + 0.03percent trifluoacetic acid over 1.5 mins) retention time 0.448 mi ESI+ found [M+H] = 231.9.
Reference: [1] Patent: WO2018/73193, 2018, A1, . Location in patent: Page/Page column 74; 75
  • 3
  • [ 74-88-4 ]
  • [ 886365-25-9 ]
YieldReaction ConditionsOperation in experiment
77% With silver (II) carbonate In toluene at 50℃; for 15 h; To a solution of methyl 5-bromo-2-hydroxy-pyridine-4-carboxylate (20.0 g, 86.2 mmol) in toluene (200 mL) was added silver carbonate (30.9 g, 112.1 mmol) and iodomethane (18.4 g, 129.3 mmol). The reaction mixture was stirred at 50 °C for 15 h and filtered. The filtrate was concentrated under reduced pressure. The residue was purified bycolumn chromatography (silica gel, 100-200 mesh, 0 to 30percent ethyl acetate in petroleum ether) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (16.4g, 77percent) as a white solid, used as is in the next step.
Reference: [1] Patent: WO2018/73193, 2018, A1, . Location in patent: Page/Page column 74
  • 4
  • [ 67-56-1 ]
  • [ 936011-17-5 ]
  • [ 886365-25-9 ]
YieldReaction ConditionsOperation in experiment
14.9 g at 0℃; for 1 h; To a solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (23.5 g, 108.8 mmol) in MeOH (100 mL) were successively added a solution of I2 (35.9 mg, 141.4 mmol) in MeOH (75 mL) and a solution of KOH (15.9 g, 282.8 mmol) in MeOH (75 mL) at 0 °C. The resulting mixture was stirred for 1 hr at 0 °C and the reaction was quenched with saturated aqueous NaHS03. The resulting mixture was diluted with DCM (400 mL). The separated organic phase was washed with H20 (150 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column (eluting with PE:EA=20: 1, v:v) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (14.9 g) as a light yellow solid.
Reference: [1] Patent: WO2018/83136, 2018, A1, . Location in patent: Page/Page column 38
  • 5
  • [ 67-56-1 ]
  • [ 886365-22-6 ]
  • [ 886365-25-9 ]
Reference: [1] Patent: US2014/94456, 2014, A1, . Location in patent: Paragraph 0925-026
[2] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0717
  • 6
  • [ 13472-85-0 ]
  • [ 886365-25-9 ]
Reference: [1] Patent: US2014/94456, 2014, A1,
[2] Patent: WO2015/153683, 2015, A1,
[3] Patent: WO2018/83136, 2018, A1,
  • 7
  • [ 936011-17-5 ]
  • [ 886365-25-9 ]
Reference: [1] Patent: US2014/94456, 2014, A1,
[2] Patent: WO2015/153683, 2015, A1,
  • 8
  • [ 886365-25-9 ]
  • [ 913836-16-5 ]
Reference: [1] Patent: US2014/94456, 2014, A1, . Location in patent: Paragraph 0925-026
[2] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0717
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