Diisopropylethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-fluorophenoxy)benzamide

HRID 1777700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777700
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH2:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH:31][C:10](=[O:12])[C:9]1[CH:8]=[CH:7][C:6]([O:5][C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[CH:3]=2)=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225734424-(3-Fluorophenoxy)benzoic acid

Produkt 1

HCID 67974035N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-fluorophenoxy)benzamideAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(3-fluorophenoxy)benzoic acid (0.180 g, 0.775 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.180 g; 0.775 mmol), HATU (0.324 g; 0.852 mmol) and N,N-diisopropylethylamine (0.334 mL; 1.94 mmol) in DMF (5 mL), was stirred at room temperature 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 by flash chromatography on silica (eluent 2 to 20% ethyl acetate in dichloromethane and 20 to 100% ethyl acetate in heptane) to yield 0.065 g (20%) 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 by flash chromatography on silica (eluent 2 to 20% ethyl acetate in dichloromethane and 20 to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-c31136d654284f9da85f89c650bdc38c
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266832B2

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