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Water → 4-Bromo-6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indole

HRID 244701
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244701
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15].O>CN(C=O)C>[Br:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:23]([C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=1)(=[O:24])=[O:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 247281734-Bromo-6-fluoro-1H-indole

Produkt 1

HCID 583563704-Bromo-6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (299 mg, 7.48 mmol) was added to a stirred solution of 4-bromo-6-fluoro-1H-indole (800 mg, 3.74 mmol) in DMF (20 ml) that had been cooled in an ice bath to 0° C. and placed under nitrogen. The mixture was stirred for 5 mins before 4-nitrobenzenesulfonyl chloride (911 mg, 4.11 mmol) was added. The mixture was stirred at 0° C. for 1 hour. The resultant orange/brown solution was poured into stirring water (40 ml). The mixture was rapidly stirred for 30 mins. The resulting brown suspension was collected by filtration, washed with water and dried in a vacuum oven at 50° C. overnight to give a pale brown solid, which was purified by Flashmaster II, on a silica cartridge (100 g) using a gradient of ethylacetate and cyclohexane to afford the title compound as a white solid.

Aufarbeitung

  1. additionwas added
  2. additionThe resultant orange/brown solution was poured
  3. stirringThe mixture was rapidly stirred for 30 mins
  4. filtrationThe resulting brown suspension was collected by filtration
  5. washwashed with water
  6. customdried in a vacuum oven at 50° C. overnight
  7. customto give a pale brown solid, which
  8. customwas purified by Flashmaster II, on a silica cartridge (100 g)

Quellen und Nachweise

ORD-Eintrag
ord-4a4491a12c2d4367af253cc6622818af
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658635B2

Notizen zur Reaktion

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