Identification | Back Directory | [Name]
5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1H-Indazole | [CAS]
1254473-74-9 | [Synonyms]
5-((tert-butyldimethylsilyl)oxy)-1H-indazole 5-(tert-butyl-dimethyl-silanyloxy)-1H-indazole 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1H-Indazole 1H-Indazole, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]- | [Molecular Formula]
C13H20N2OSi | [MOL File]
1254473-74-9.mol | [Molecular Weight]
248.4 |
Questions And Answer | Back Directory | [Synthesis]
1H-indazol-5-ol (1.00 g, 7.45 mmol)
dissolved in 20 mL of anhydrous methylene chloride was added to a 100 mL round bottom flask.
Tert-butyldimethylsilyl chloride (1.69 g, 11.18 mmol) and imidazole (0.51 g, 7.45 mmol) were
added to the reaction vessel producing a cloudy white mixture. Lastly, N,Ndiisopropylethylamine
(1.95 mL, 11.18 mmol) was added, giving a clear solution. The reaction
was stirred overnight at room temperature.
Methylene chloride was used to dilute the reaction
followed by washing with NaCl (2x). The organic layer was dried over MgSO4, concentrated in
vacuo, and purified using flash chromatography with a 20% EtOAc/Hexane gradient to give 5-
((tert-butyldimethylsilyl)oxy)-1H-indazole (5a) (1.72g, 93%). 1H NMR (DMSO – d6, 400 MHz)
δ: 12.91 (s, 1H), 7.92 (s, 1H), 7.41 (d, J=9.0 Hz, 1H), 7.12 (d, J=1.5 Hz, 1H), 6.91 (dd, J = 8.8,
2.3 Hz, 1H), 0.96 (s, 9H), 0.18 (s, 6H). |
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