Sodium Bicarbonate → tert-butyl 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate

HRID 1673497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673497
[N:1]1([C:6]2[CH:7]=[C:8]([C:12](Cl)=[O:13])[CH:9]=[N:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[NH2:15][C:16]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl>[C:29]1([C:27]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])=[C:16]([NH:15][C:12]([C:8]3[CH:9]=[N:10][CH:11]=[C:6]([N:1]4[CH:5]=[CH:4][CH:3]=[CH:2]4)[CH:7]=3)=[O:13])[CH:28]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylateHCID 862468235-(1H-pyrrol-1-yl)pyridine-3-carbonyl chloride2×

Produkt 1

HCID 67342180tert-butyl 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

0.062 mL of triethylamine and 69 mg of 5-(1H-pyrrol-1-yl)pyridine-3-carbonyl chloride were added to 5.0 mL of methylene chloride solution containing 60 mg of tert-butyl 2-amino-4-phenylbenzoate at room temperature sequentially and stirred at the same temperature for 2 hours. 0.031 mL of triethylamine and 23 mg of 5-(1H-pyrrol-1-yl)pyridine-3-carbonyl chloride were added to the reaction mixture at room temperature sequentially and stirred at the same temperature for 1 hour. 0.62 g of aminomethylated polystyrene was added to the reaction mixture and stirred at room temperature overnight. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1] to obtain tert-butyl 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate.

Aufarbeitung

  1. stirringstirred at the same temperature for 1 hour
  2. stirringstirred at room temperature overnight
  3. customthe organic layer was separated
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]

Quellen und Nachweise

ORD-Eintrag
ord-e11c9a2a307b455382c1bbb63f8e77b7
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999132B2

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