5-Indolylboronic acid → US9814704, Example 20

HRID 85015

Reaktionsgleichung

Reaktionsgleichung von HRID 85015
[NH:1]1C2C(=CC(B(O)O)=CC=2)C=C1.Br[C:14]1[CH:15]=[C:16]2[C:22](I)=[CH:21][N:20](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]2=[N:18][CH:19]=1.[NH2:34][C:35]1[N:40]=[CH:39][C:38](B(O)O)=[CH:37][N:36]=1.COC1C=C(B(O)O)C=C(OC)C=1OC.BrC1C=C2[C:68]([C:69]3C=C4C(=CC=3)NC=C4)=[CH:67][N:66](S(C3C=CC(C)=CC=3)(=O)=O)[C:63]2=[N:64]C=1>>[NH:20]1[C:17]2=[N:18][CH:19]=[C:14]([C:38]3[CH:37]=[N:36][C:35]([NH2:34])=[N:40][CH:39]=3)[CH:15]=[C:16]2[C:22]([C:68]2[CH:69]=[N:1][C:63]([NH2:64])=[N:66][CH:67]=2)=[CH:21]1

Komponenten

6

Edukt 5

HCID 27343615-Indolylboronic acidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 66779903US9814704, Example 20

Versuchsvorschrift

Compound W was prepared by a method analogous to that described in Example 1 by substituting 2-aminopyrimidin-5-ylboronic acid for 1H-indol-5-ylboronic acid in the reaction with Intermediate A and 2-aminopyrimidin-5-ylboronic acid for 3,4,5-trimethoxyphenylboronic acid in the reaction with Intermediate B. HPLC retention time: 1.17 minutes. MS ESI (m/z): 305.2 (M+H)+, calc. 304.

Quellen und Nachweise

ORD-Eintrag
ord-7bb733119f274e7eb823eb22cb7ce4d2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846909B2

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