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Chemical Structure| 364793-54-4 Chemical Structure| 364793-54-4
Chemical Structure| 364793-54-4

6-Bromo-4-chloro-quinoline-3-carbonitrile

CAS No.: 364793-54-4

4.5 *For Research Use Only !

Cat. No.: A732742 Purity: 98%

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Product Details of [ 364793-54-4 ]

CAS No. :364793-54-4
Formula : C10H4BrClN2
M.W : 267.51
SMILES Code : N#CC1=C(Cl)C2=CC(Br)=CC=C2N=C1
MDL No. :MFCD09261323
InChI Key :OCILRHPBZATKKG-UHFFFAOYSA-N
Pubchem ID :23438095

Safety of [ 364793-54-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 364793-54-4 ]

* 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.

  • Downstream synthetic route of [ 364793-54-4 ]

[ 364793-54-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 102877-78-1 ]
  • [ 364793-54-4 ]
  • 6-bromo-4-((4-(pyridin-4-yloxy)phenyl)amino)quinoline-3-carbonitrile hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In 2-ethoxy-ethanol; at 125℃; for 2h;Sealed tube; A mixture consisting of 6-bromo-4-chloroquinoline-3-carbonitrile (440 mg, 1.64 mmol) and <strong>[102877-78-1]4-(pyridin-4-yloxy)aniline</strong> (291 mg, 1.56 mmol) in 3 mL of ethoxyethanol was heated at 125 Cfor 2 hours in a sealed vessel. The reaction mixture was cooled to room temperature and filteredto give 193 mg of the title compound as a light brown solid. The filtrate was diluted with ethylacetate and washed with a saturated solution of sodium bicarbonate. The aqueous phase was extracted two time with ethyl acetate. The combined organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on 25 g of silica eluted with a gradient of 45:55 ethyl acetate-heptane to 100%ethyl acetate to 2:98 methanol-ethyl acetate to give 160 mg of the title compound as a tan solid. Total: 353 mg (54%,). A sample of the light brown solid was mostly dissolved in 5 mL of 2:8 methanol-dichloromethane and while stirring 15 mL of diethyl ether and 5 mL of heptane were added. The suspension was stirred overnight and filtered. The filtrate was set at room temperature and the crystalline material which formed was filtered to give near white solid(99.9% pure); MS (ES-API+) m/z 417.0 (M+1) 419.0 (Br isotope), (ES-API-) m/z 414.9 (M-1)417.0 (Br isotope); ?H NMR (400 MHz, DMSO-d6) oe 10.03 (br s, 1H), 8.78 (d, J1.92 Hz, 1H),8.57 (s, 1H), 8.44-8.51 (m, 2H), 7.97(dd,J=2.10, 8.87 Hz, 1H), 7.85 (d,J=8.87Hz, 1H), 7.45(d, J=8.69 Hz, 2H), 7.2 1-7.30 (m, 2H), 6. 97-7.03 (m, 2H).
  • 2
  • [ 1083326-75-3 ]
  • [ 364793-54-4 ]
  • N-(5-(4-chloro-3-cyanoquinolin-6-yl)-2-methoxypyridin-3-yl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 7h;Inert atmosphere; 6-Bromo-4-chloroquinoline-3-carbonitrile (140 mg, 0.6 mmol), N- (2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Pyridin-3-yl)Methanesulfonamide (203 mg, 0.618 mmol, 1.03 eq) and 2N aqueous potassium carbonate solution (0.9 mL, 1.8 mmol, 3.0 eq) in dioxane (6 mL) was degassed and bis (triphenylphosphine) dichloropalladium (21 mg, 0.03 mmol, 0.05 eq ). The resulting reaction mixture was degassed and backfilled with argon (three cycles) and then stirred at 100degC under argon for 7 hours.The reaction mixture was cooled to room temperature, diluted with water (30 mL) and extracted with ethyl acetate (30 mL x 3). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography (silica gel, dichloromethane / methanol = 350: 1, v / v)To give a yellow solid (82 mg, 35% yield).
 

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Related Parent Nucleus of
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