Tributyltin Chloride → 6-fluoro-3-(tributylstannyl)-1H-indazole

HRID 246633

Reaktionsgleichung

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:17]([Sn:21]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])Cl)[CH2:18][CH2:19][CH3:20]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:21]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:17][CH2:18][CH2:19][CH3:20])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

6-Fluoro-3-iodo-1H-indazole (300 mg, 1.1 mmol) in 30 mL of dry THF was cooled to −20° C. under nitrogen atmosphere, then isopropylmagnesium chloride (1.2 mL, 2.42 mmol) was added and mixture stirred for 15 mins at −20° C. Tributylchlorostannane (0.4 mL, 1.32 mmol) was added and the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction was quenched with saturated ammonium chloride, product extracted with ethyl acetate (3×50 mL), dried with sodium sulphate, filtered and concentrated to give 6-fluoro-3-(tributylstannyl)-1H-indazole (500 mg, crude) as a colorless oil which was used directly in the next step without further purification.

Aufarbeitung

temperatureto warm to room temperature
stirringstirred for 1 h
customThe reaction was quenched with saturated ammonium chloride, product
extractionextracted with ethyl acetate (3×50 mL)
dry with materialdried with sodium sulphate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-29cd64a8d8eb4cdda7c870258d170685
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658646B2

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