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Chemical Structure| 426842-84-4 Chemical Structure| 426842-84-4

Structure of 426842-84-4

Chemical Structure| 426842-84-4

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Product Details of [ 426842-84-4 ]

CAS No. :426842-84-4
Formula : C10H7FINO
M.W : 303.07
SMILES Code : COC1=CC=C2N=CC(F)=C(I)C2=C1

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Application In Synthesis of [ 426842-84-4 ]

* 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 [ 426842-84-4 ]

[ 426842-84-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 72287-26-4 ]
  • potassium phosphate [ No CAS ]
  • [ 426842-84-4 ]
  • [ 280-64-8 ]
  • [ 146603-99-8 ]
  • ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; ethyl acetate; Ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate 1.4 g of ethyl 4-allyl-1-(tert-butyloxy-carbonyl)piperidine-4-carboxylate were cooled to a temperature in the region of -30° C. and 11 cm3 of a 0.5 M 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. The solution obtained was stirred for a further 4 hours, followed by addition of 0.09 g of palladium diphenylphosphinoferrocene chloride, 1.4 g of 4-iodo-3-fluoro-6-methoxyquinoline and 2.5 g of tribasic potassium phosphate. After stirring for 16 hours at a temperature in the region of 60° C., the reaction mixture was cooled to about 20° C. and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was taken up in ethyl acetate and water, the phases were separated by settling and 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 40° C. The residue obtained was purified by chromatography, under atmospheric pressure, on a column of silica gel (particle size 70-200 mu; diameter 4.5 cm; mass 125 g), eluding with a mixture of dichloromethane/ethyl acetate (98/2 by volume), and collecting 20-cm3 fractions. Fractions 98 to 170 were combined and then concentrated to dryness under the above conditions. 1.5 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate were obtained in the form of a thick brown oil. 1H NMR Spectrum (300 MHz, (CD3)2SO-d6, 6 in ppm): 1.02 (t, J=7 Hz: 3H); 1.30 (mt:2H); 1.39 (s: 9H); from 1.45 to 1.70 (mt: 4H); 1.92 (broad d, J=13.5 Hz: 2H); 2.81 (mt: 2H); 3.05 (broad t, J=6.5 Hz: 2H); 3.69 (broad d, J=13.5 Hz: 2H); 3.95 (s: 3H); 4.00 (q, J=7 Hz: 2H); 7.34 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70 (d, J=1 Hz: 1H).
 

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