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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → HCID 66685755, Verbindung

HRID 1778402
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1778402
[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:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([NH2:24])[CH:17]=[CH:16][C:15]=1[C:25]1[CH:29]=[CH:28][O:27][C:26]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(Cl)Cl.N1C=CC=CC=1>[NH2:13][C:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([NH:24][S:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Br:1])(=[O:11])=[O:10])[CH:17]=[CH:16][C:15]=1[C:25]1[CH:29]=[CH:28][O:27][C:26]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride3×HCID 66685481Ethyl 3-(2,4-diamino-3-methoxycarbonylphenyl)-furan-2-carboxylate2×

Produkt 1

HCID 66685755HCID 66685755, VerbindungAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

2-Bromo-4-fluorobenzenesulfonyl chloride (0.584 g) was added to a solution of ethyl 3-(2,4-diamino-3-methoxycarbonylphenyl)-furan-2-carboxylate (Intermediate 89, 0.650 g) in DCM (30 mL) and pyridine (10 mL). The resultant mixture was stirred at room temperature for 45 minutes. A further amount of 2-bromo-4-fluorobenzene-sulfonyl chloride (0.584 g) was added and the mixture stirred for a further 1 hour. A further amount of 2-bromo-4-fluorobenzenesulfonyl chloride (0.300 g) was added and the mixture stirred for a further 30 minutes. The mixture was concentrated in vacuo and the residue was partitioned between water and DCM. The organic layer was dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was triturated with methanol and the resultant solid was collected by filtration and air dried to give ethyl 3-[2-amino-4-(2-bromo-4-fluorobenzenesulfonylamino)-3-methoxycarbonylphenyl]-furan-2-carboxylate (0.960 g) as a powder.

Aufarbeitung

  1. stirringthe mixture stirred for a further 30 minutes
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and DCM
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was triturated with methanol
  8. filtrationthe resultant solid was collected by filtration and air
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e4d3c2ad457545b38b76b2634a8eb6bc
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266896B2

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