N-Iodosuccinimide → HCID 178455023, Verbindung

HRID 1053634

Reaktionsgleichung

Reaktionsgleichung von HRID 1053634
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([I:25])C(=O)C1>CN(C)C=O>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[I:25])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

Produkt 1

HCID 178455023HCID 178455023, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-[(tert-butyldimethylsilyl)oxy]-1H-indazole (13 g, 52.34 mmol, 1.00 equiv) in N,N-dimethylformamide (550 mL) maintained under nitrogen was added NIS (28.6 g, 104.76 mmol, 2.00 equiv) in portions. The reaction mixture was stirred at room temperature overnight and then concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-10% of ethyl acetate in petroleum ether to give 19.2 g (98%) of 5-(tert-butyldimethylsilyloxy)-3-iodo-1H-indazole as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 7.50-7.45 (m, 1H), 7.09 (dd, J=9.0 Hz, 2.1 Hz, 1H), 6.98-6.70 (m, 1H), 1.10 (s, 9H), 0.24 (s, 6H) ppm. LCMS (method A, ESI): RT=1.80 min, m/z=374.9 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified on a silica gel column
  3. washeluted with 0-10% of ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-eb793d94eabb4d009c81ff497987b181
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394258B2

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