Reaktion #333825

Reaktionsgleichung

NH4Cl

tributylchlorostannane

6-chloro-3-iodo-1H-indazole

isopropylmagnesium chloride

→

6-chloro-3-(tributylstannyl)-1H-indazole

Ausbeute 77.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionproduct extracted with dichloromethane (15 mL), organic phase
2. 2
   Waschenwas washed with water (2×20 mL) and brine (2×20 mL)
3. 3
   TrocknenThe organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated

Vorschrift

To a solution of 6-chloro-3-iodo-1H-indazole (337 mg, 1.21 mmol) in dry tetrahydrofuran (20 mL) was added drop-wise isopropylmagnesium chloride (1.33 mL, 2M in THF, 2.66 mmol) at −16° C. under N2 atmosphere. After stirring for 20 minutes, tributylchlorostannane (472 mg, 1.45 mmol) was added drop-wise at −16° C., and then it was warmed to 20° C. for 2 h. Then NH4Cl solution (2 mL) was added and product extracted with dichloromethane (15 mL), organic phase was washed with water (2×20 mL) and brine (2×20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to afford 6-chloro-3-(tributylstannyl)-1H-indazole (413 mg, crude) as yellow oil which was used to next step without further purification.

Quelle