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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate

HRID 1778337
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1778337
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]2[C:17]([C:18]3[CH:30]=[CH:29][O:28][C:19]=3[CH:20]=[N:21]2)=[CH:16][CH:15]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:13][C:14]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]2[C:17]([C:18]3[CH:30]=[CH:29][O:28][C:19]=3[CH:20]=[N:21]2)=[CH:16][CH:15]=1)(=[O:11])=[O:10]
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Komponenten

4

Edukt 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride2×HCID 66685912Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate2×

Produkt 1

HCID 66685289Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylateAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 2-bromo-4-fluorobenzenesulfonyl chloride (0.57 g) in pyridine (10 mL) was heated to 70° C. and a solution of methyl 7-amino-furo[2,3-c]quinoline-6-carboxylate (Intermediate 16, 0.33 g) in pyridine (10 mL) was added. The mixture was stirred and heated at 70° C. for 4 hours. Further 2-bromo-4-fluorobenzenesulfonyl chloride (0.57 g) was added and the mixture was stirred and heated at 70° C. overnight. After cooling, the mixture was filtered and the solid was washed with methanol. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-60%. The product was triturated with diethyl ether and the solid was collected by filtration to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate (0.16 g) as a yellow solid.

Aufarbeitung

  1. stirringthe mixture was stirred
  2. temperatureheated at 70° C. overnight
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washthe solid was washed with methanol
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-60%
  9. customThe product was triturated with diethyl ether
  10. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5687ad9c6ba94877852d1ea388dc9d65
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266896B2

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