1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one → (rac)-N-(4-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 530349

Reaktionsgleichung

Reaktionsgleichung von HRID 530349
Br[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=2[CH:5]=[N:6][CH:7]=1.[CH3:16][N:17]1[C:26]2[C:21](=[CH:22][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:25]=2)[CH2:20][CH2:19][C:18]1=[O:36]>>[CH3:16][N:17]1[C:26]2[C:21](=[CH:22][C:23]([C:2]3[C:3]4[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=4[CH:5]=[N:6][CH:7]=3)=[CH:24][CH:25]=2)[CH2:20][CH2:19][C:18]1=[O:36]

Komponenten

3

Edukt 2

HCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

Produkt 1

HCID 71536225(rac)-N-(4-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideAusbeute 87 %

Versuchsvorschrift

In analogy to the procedure described for the preparation of intermediate A-2 [E], (rac)-N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide (intermediate A-3) was reacted with 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one (intermediate A-1) to give the title compound as an off-white powder in 87% yield. MS: 350.2 (M+H+).

Quellen und Nachweise

ORD-Eintrag
ord-6735acaa9ae4434bb55f7bd1a5b7b651
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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