2-Chloropyridine-4-boronic acid, pinacol ester → N-(5-(2-chloropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide

HRID 1924785

Reaktionsgleichung

Reaktionsgleichung von HRID 1924785
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:23])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[CH:27][N:26]=1>>[Cl:24][C:25]1[CH:30]=[C:29]([C:2]2[N:7]=[C:6]3[S:8][C:9]([NH:11][C:12](=[O:23])[C:13]4[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=4)=[N:10][C:5]3=[CH:4][CH:3]=2)[CH:28]=[CH:27][N:26]=1

Komponenten

3

Edukt 2

HCID 51034082-Chloropyridine-4-boronic acid, pinacol esterHCID 58015365HCID 58015365, Verbindung

Produkt 1

HCID 44548455N-(5-(2-chloropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamideAusbeute 43 %

Versuchsvorschrift

The titled compound (yield=43%, yellow solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 1D (Example 1) and 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (s, 6H) 5.24 (s, 1H) 7.67 (d, J=8.34 Hz, 2H) 8.12 (d, J=8.34 Hz, 2H) 8.18 (d, J=5.56 Hz, 1H) 8.25 (s, 1H) 8.28-8.37 (m, 2H) 8.55 (d, J=5.31 Hz, 1H) 13.12 (s, 1H); ESI-MS: m/z 425.0 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-86c895254ed74cdd9c68b60a37901f0d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178555B2

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