PyBOP → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(2-fluorophenyl)-2-oxopyrrolidine-3-carboxamide

HRID 1918692

Reaktionsgleichung

Reaktionsgleichung von HRID 1918692
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[F:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[N:55]1[CH2:59][CH2:58][CH:57]([C:60](O)=[O:61])[C:56]1=[O:63]>CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:60]([CH:57]1[CH2:58][CH2:59][N:55]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2[F:48])[C:56]1=[O:63])=[O:61]

Komponenten

5

Edukt 3

HCID 2724699PyBOPHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 45691531-(2-Fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acid

Produkt 1

HCID 66831906N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-(2-fluorophenyl)-2-oxopyrrolidine-3-carboxamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.104 g; 0.448 mmol), PyBOP (0.349 g; 0.672 mmol), N,N-diisoprpylethylamine (0.232 mL; 1.34 mmol) and 1-(2-fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid (0.100 g; 0.448 mmol) was stirred in DMF (3 mL) overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.078 g (44%) of the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-a409813d26964b36bad22b9a50bac95e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618138B2

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