Methyl iodide → 5-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole

HRID 245952

Reaktionsgleichung

[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[I:16])([CH3:4])([CH3:3])[CH3:2].[CH3:19]C(C)([O-])C.[K+].CI>C1COCC1>[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:19])[N:11]=[C:10]2[I:16])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

In a round-bottomed flask, 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1H-indazole (1.65 g, 4.41 mmol) was dissolved in THF (16 ml). The solution was cooled to 0° C. and potassium tert-butoxide (697 mg, 6.22 mmol) was added. The reaction mixture was stirred at 0° C. for 30 min then methyl iodide (0.38 ml, 6.08 mmol) was added dropwise. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 4.5 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-10% EtOAc) to give 770 mg (45%) of 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1-methyl-1H-indazole as a light yellow solid.

Aufarbeitung

additionAfter the addition
customthe ice bath was removed
stirringthe reaction mixture was stirred at room temperature for 4.5 h
customThe reaction was quenched with water
extractionextracted with EtOAc (2×)
washThe combined organic layers were washed with water and brine
dry with materialthen dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-10% EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-2f4e756a8ff646c388a9d3e5f335b719
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658646B2

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