N-(6,6-dimethyl bicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzenesulphonamide → 2,2,2-Trifluoro-1-(1-(3-(4-(4-hydroxybutyl)phenyl)propyl)-1H-indol-3-yl)ethanone

HRID 717646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717646
[F:1][C:2]([F:29])([F:28])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH2:25][CH2:26][OH:27])=[CH:19][CH:18]=2)[CH:6]=1)=[O:4].CC1(C)C2CC1CCC2NS(C1C=CC(C#CCCO)=CC=1)(=O)=O>>[F:29][C:2]([F:1])([F:28])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:21][CH:22]=2)[CH:6]=1)=[O:4]

Komponenten

3

Edukt 2

HCID 66614933N-(6,6-dimethyl bicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzenesulphonamideHCID 680020402,2,2-Trifluoro-1-(1-(3-(4-(4-hydroxybut-1-ynyl)phenyl)prop-2-ynyl)-1H-indol-3-yl)ethanone

Produkt 1

HCID 666148842,2,2-Trifluoro-1-(1-(3-(4-(4-hydroxybutyl)phenyl)propyl)-1H-indol-3-yl)ethanoneAusbeute 92 %

Versuchsvorschrift

When the product of Step D was substituted for N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-4-(4-hydroxybut-1-ynyl)benzene sulphonamide in Example 18, Step C, the identical process afforded the title compound in 92% yield, as pale paste. 1H-NMR (CDCl3) 8.40 (broad s, 1H); 7.86 (s, 1H); 7.37-7.32 (m, 3H); 7.11 (d, 2H, J=8.07 Hz); 7.05 (d, 2H, J=8.07 Hz); 4.19 (t, 2H, J=7.17 Hz); 3.72-3.63 (m, 4H); 2.66-2.59 (m, 4H); 1.68-1.60 (m, 4H).

Quellen und Nachweise

ORD-Eintrag
ord-def264de01454b5289a9f6a82c0dcd44
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193716B2

Notizen zur Reaktion

Wird geladen…