Toluene → 6-cyclopropyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 245804

Reaktionsgleichung

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:19]1([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][N:8]3[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=2)[CH2:21][CH2:20]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A round-bottomed flask was charged with 6-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (0.80 g, 2.44 mmol), cyclopropylboronic acid (377 mg, 4.39 mmol), palladium(II) acetate (28 mg, 0.125 mmol), potassium phosphate tribasic (1.04 g, 4.88 mmol), toluene (9 ml) and water (0.9 ml). The reaction mixture was stirred at 100° C. in an oil bath overnight then cooled to room temperature, 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 0-5% EtOAc) to afford 670 mg (90%) of 6-cyclopropyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole as a light yellow oil.

Aufarbeitung

temperaturethen cooled to room temperature
customquenched 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 0-5% EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-c18be89c1d6c4caba5d0593ea777c4b6
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658646B2

Verknüpfte Notizen

Wird geladen…