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Chemical Structure| 213772-63-5 Chemical Structure| 213772-63-5

Structure of 213772-63-5

Chemical Structure| 213772-63-5

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Product Details of [ 213772-63-5 ]

CAS No. :213772-63-5
Formula : C9H5FIN
M.W : 273.05
SMILES Code : IC1=C(F)C=NC2=CC=CC=C12
MDL No. :MFCD03093328
InChI Key :DITDYVZDDKBMGH-UHFFFAOYSA-N
Pubchem ID :11108496

Safety of [ 213772-63-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H311-H331
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 213772-63-5 ]

* 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 [ 213772-63-5 ]

[ 213772-63-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 396-31-6 ]
  • [ 213772-63-5 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; iodine; diisopropylamine; In tetrahydrofuran; hexane; ethyl acetate; 3-Fluoro-4-iodoquinoline 17.3 cm3 of diisopropylamine in 650 cm3 of tetrahydrofuran were cooled to a temperature in the region of -75 C. and 76 cm3 of a 1.6M solution of butyl lithium in hexane were added, with stirring and under an inert atmosphere, while maintaining the temperature at about -70 C. After stirring for 20 minutes at a temperature in the region of -75 C., a solution of 11.9 g of <strong>[396-31-6]3-fluoroquinoline</strong> in 200 cm3 of tetrahydrofuran was added. The solution obtained was stirred for a further 4 hours at -75 C., followed by addition of a solution of 32.2 g of double-sublimed iodine in 150 cm3 of tetrahydrofuran. After stirring for 2 hours at a temperature in the region of -40 C., the reaction mixture was hydrolyzed with 200 cm3 of a tetrahydrofuran/water mixture (90/10 by volume) and then with 200 cm3 of saturated sodium chloride solution. In the region of 20 C., the mixture was diluted with 300 cm3 of ethyl acetate and washed with twice 250 cm3 of saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 50C. The residue obtained was purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45 μ; diameter 10 cm; height 30 cm), eluding with dichloromethane and collecting 100-cm3 fractions. Fractions 45 to 80 were combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40 C. 15.1 g of 3-fluoro-4-iodoquinoline were obtained in the form of a cream-colored solid melting at 110 C. Mass spectrum: EI m/z=273 M+. base peak m/z 146 [M-I]+
  • 2
  • [ 72287-26-4 ]
  • potassium phosphate [ No CAS ]
  • [ 280-64-8 ]
  • [ 213772-63-5 ]
  • [ 146603-99-8 ]
  • ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate 17.7 g of ethyl 4-allyl-1-(tert-butyloxy-carbonyl)piperidine-4-carboxylate in 200 cm3 of tetrahydrofuran were cooled to a temperature in the region of -30° C. and 135 cm3 of a 0.5M solution of 9-borabicyclo-[3.3.1]nonane in tetrahydrofuran were added with stirring and under an inert atmosphere. After the addition, the temperature of the mixture was returned to about 20° C. and the mixture was stirred for 2 hours. 14.8 g of 3-fluoro-4-iodoquinoline in 430 cm3 of tetrahydrofuran, 1.3 g of palladium diphenylphosphinoferrocene chloride and 29.8 g of tribasic potassium phosphate were added. The reaction mixture was then heated at a temperature in the region of 70° C. for 20 hours. After cooling to a temperature in the region of 20° C., the reaction mass was filtered and washed with 3 times 100 cm3 of tetrahydrofuran. The filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The evaporation residue was taken up in 500 cm3 of diethyl ether, the insoluble material was washed with 3 times 100 cm3 of diethyl ether and the filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The oil obtained was purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45 mu; diameter 6 cm; height 45 cm), eluding with a dichloromethane/ethyl acetate mixture (90/10 by volume) and collecting 120-cm3 fractions. Fractions 30 to 76 were combined and then concentrated to dryness under the same conditions as above. 13.7 g of ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate were obtained in the form of a viscous orange-colored oil. Mass spectrum: EI m/z=444 M+. m/z=388 [M-tBu]+.m/z=343 [M-BOC]+m/z=288 C17H19FNO2+. m/z=184 C10H18NO2+.m/z=161 C10H8FN+m/z=57 C4H9+
 

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