4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-OL → 3,4-Dihydro-1-methyl-6-(5,6,7,8-tetrahydro-8-hydroxy-4-isoquinolinyl)-2(1H)-quinolinone

HRID 530370

Reaktionsgleichung

Reaktionsgleichung von HRID 530370
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([OH:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[CH3:13][N:14]1[C:23]2[C:18](=[CH:19][C:20](B3OC(C)(C)C(C)(C)O3)=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:33]>>[OH:12][CH:7]1[C:6]2[CH:5]=[N:4][CH:3]=[C:2]([C:20]3[CH:19]=[C:18]4[C:23](=[CH:22][CH:21]=3)[N:14]([CH3:13])[C:15](=[O:33])[CH2:16][CH2:17]4)[C:11]=2[CH2:10][CH2:9][CH2:8]1

Komponenten

3

Edukt 2

HCID 717438914-Bromo-5,6,7,8-tetrahydroisoquinolin-8-OLHCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 715068883,4-Dihydro-1-methyl-6-(5,6,7,8-tetrahydro-8-hydroxy-4-isoquinolinyl)-2(1H)-quinolinone

Versuchsvorschrift

In analogy to the procedure described for the preparation of intermediate A-2 [E], Suzuki reaction of (rac)-4-bromo-5,6,7,8-tetrahydro-isoquinolin-8-ol with 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) gave the title compound as light red powder. MS: 309.5 (M+H+).

Quellen und Nachweise

ORD-Eintrag
ord-97172c900b18493497b8d66fd5ad77ac
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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