Sodium Bicarbonate → Tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate

HRID 2191699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191699
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]([C:32](Cl)=[O:33])=[CH:24]1.C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]([C:32]([NH:1][C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)=[O:33])=[CH:24]1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 2776338Benzo(b)thiophene-3-carbonyl chlorideHCID 68958505Tert-butyl 4-amino-2-(4-fluoroanilino)benzoate

Produkt 1

HCID 68959063Tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To dichloromethane 3.0 mL solution of tert-butyl 4-amino-2-(4-fluoroanilino)benzoate 40 mg were added triethylamine 0.064 mL, benzothiophene-3-carbonyl chloride 55 mg and dichloromethane 1.5 mL at room temperature, and it was stirred at same temperature for 2 hours. Aminomethylated-polystyrene 250 mg was added to the reaction mixture, and it was stirred at room temperature for 4 hours. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and insoluble matter was filtrated. The organic layer was separated and collected, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 4-(benzothiophene-3-carboxamido)-2-(4-fluoroanilino)benzoate.

Aufarbeitung

  1. stirringwas stirred at room temperature for 4 hours
  2. filtrationwas filtrated
  3. customThe organic layer was separated
  4. customcollected
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-19b302fce4034fc4b65c6e7619158580
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08327467B2

Notizen zur Reaktion

Wird geladen…