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[ CAS No. 886365-47-5 ]

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Chemical Structure| 886365-47-5
Chemical Structure| 886365-47-5
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CAS No. :886365-47-5 MDL No. :MFCD08436181
Formula : C7H5BrClNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :234.48 g/mol Pubchem ID :25417865
Synonyms :

Safety of [ 886365-47-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886365-47-5 ]

  • Upstream synthesis route of [ 886365-47-5 ]
  • Downstream synthetic route of [ 886365-47-5 ]

[ 886365-47-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 885223-63-2 ]
  • [ 886365-47-5 ]
YieldReaction ConditionsOperation in experiment
90% With methylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 0.5 h; Inert atmosphere To a solution of compound 12b (2.0 g, 7.15 mmol) in anhydrous THF (15mL) was added methylmagnesium bromide (1M in THF, 8 mL, 8 mmol) dropwise at 0 °C under Argon atmosphere. The resulting mixture was stirred at room temperature for 30 min. The reaction was quenched with sat. NH4Cl solution, diluted with water (50 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 6:1, v/v) to give the title compound 12c (1.5 g, 90percent yield) as a yellow solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 790 - 793
  • 2
  • [ 1111638-41-5 ]
  • [ 886365-47-5 ]
YieldReaction ConditionsOperation in experiment
77% With pyridine; chromium(VI) oxide In dichloromethane at 0 - 20℃; Silica gel Preparation of 1-(5-bromo-2-chloropyridin-3-yl)ethanone (D-2-5). <n="106"/>To a stirred solution of pyridine (13 g, 0.165 mol) in CH2CI2 (200 mL) was added CrO3 (8.25 g, 0.083 mol) and silica gel (20 mL) portionwise at 0 °C. After the addition, the reaction mixture was stirred for 10 minutes. Compound D-2-4 (6.5 g, 27.5 mmol) was then added and the resulting mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 8:1 ) indicated most of compound D-2-4 was consumed. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give crude compound D-2-5, which was purified by column chromatography (silica gel petroleum ether/EtOAc 20:1) to give pure compound D-2-5 (5 g, yield: 77percent) as a yellow oil.
Reference: [1] Patent: WO2009/16460, 2009, A2, . Location in patent: Page/Page column 104-105
  • 3
  • [ 885223-63-2 ]
  • [ 75-16-1 ]
  • [ 886365-47-5 ]
YieldReaction ConditionsOperation in experiment
90% at 0 - 20℃; for 0.5 h; Inert atmosphere To a solution of compound4(2.0 g, 7.15 mmol) in anhydrous THF (15mL) was addedmethylmagnesium bromide(1M in THF, 8 mL, 8 mmol) dropwise at 0°Cunderargon atmosphere. The resulting mixture was stirred at room temperaturefor 30 min. The reaction was quenched with sat. NH4Cl solution,diluted withwater(50 mL) and extracted with ethyl acetate (50 mL×3).The combined organic layers werewashed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1, v/v) to give the title compound5as a yellow solid(1.5 g, 90percent yield). 1H NMR (400 MHz, DMSO-d6) δ 8.71 (d,J= 2.5 Hz, 1H), 8.46 (d,J= 2.5 Hz, 1H), 2.62 (s, 3H).
54.3% at -78℃; for 3 h; Starting material 5-bromo-2- chloro-N-methoxy-N-methylnicotinamide (5.0 g, 17.89 mmol) was charged into a 250 ml round bottom flask and the flask was chilled to -78 0C. Methyl magnesium bromide 96.5 ml, 19.68 mmol) in 5 ml THF was added dropwise via addition funnel. The resulting mixture was allowed to stir for 3 hours at -78 0C. After removing the THF solvent via rotatory evaporation under reduced pressure, the reaction mixture was partitioned between ethylacetate and saturated aqueous sodium bicarbonate. After removing the ethylacetate, the resulting crude product was subject to a silica gel column with 20percent ethylacetate in hexane. The resulting product (2.28 g, y=54.3percent) was used for the following step.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4538 - 4541
[2] Patent: WO2006/44860, 2006, A2, . Location in patent: Page/Page column 43-44
  • 4
  • [ 885223-63-2 ]
  • [ 676-58-4 ]
  • [ 886365-47-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5578 - 5585
  • 5
  • [ 29241-65-4 ]
  • [ 886365-47-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5578 - 5585
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 790 - 793
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4538 - 4541
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