Imidazole → 5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

HRID 1053633

Reaktionsgleichung

Reaktionsgleichung von HRID 1053633
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[Si:20]([O:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1014381H-Indazol-5-ol

Produkt 1

HCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazoleAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1H-indazol-5-ol (25 g, 186.38 mmol, 1.00 equiv), imidazole (31.7 g, 466.18 mmol, 2.50 equiv) and tert-butyl(chloro)dimethylsilane (33.8 g, 224.25 mmol, 1.20 equiv) in N,N-dimethylformamide (100 mL) was stirred at room temperature for 2 h. The reaction was quenched by the addition of water/ice (200 mL). The precipitate was collected by filtration and dried in a vacuum oven to give 45 g (97%) of 5-(tert-butyldimethylsilyloxy)-1H-indazole as a brown solid. 1H NMR (300 MHz, CDCl3): δ 8.00 (s, 1H), 7.40 (d, J=9.0 Hz, 1H), 7.15 (d, J=9.0 Hz, 1H), 7.02 (dd, J=9.0 Hz, 2.4 Hz, 1H), 1.03 (s, 9H), 0.24 (s, 6H) ppm. LCMS (method D, ESI): RT=1.66 min, m/z=249.0 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched by the addition of water/ice (200 mL)
  2. filtrationThe precipitate was collected by filtration
  3. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-36f93e63a16449cdb6aaef4c78193b02
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394258B2

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