Reaktion #333778

Reaktionsgleichung

chlorotributyltin

3-iodo-1-methyl-1H-indazole-6-carbonitrile

3-iodo-2-methyl-1H-indazole-6-carbonitrile

Isopropylmagnesium chloride

→

1-Methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.STIRRINGstirred for 1.5 h
3. 3
   SonstigeThe reaction mixture was quenched with saturated NH4Cl solution
4. 4
   Extraktionextracted with EtOAc (3×5 mL)
5. 5
   Waschenorganics were washed with water (10 mL), brine (2×10 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was used to the next step without further purification

Vorschrift

The crude mixture of 3-iodo-1-methyl-1H-indazole-6-carbonitrile and 3-iodo-2-methyl-1H-indazole-6-carbonitrile (97 mg, crude) was dissolved in THF (4 mL). The solution was cooled to −40° C. Isopropylmagnesium chloride (0.21 mL, 0.41 mmol, 2M in THF) was added drop-wise at −40° C. The reaction mixture was stirred at −40° C. for 20 min. Then chlorotributyltin (0.11 mL) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was quenched with saturated NH4Cl solution and then extracted with EtOAc (3×5 mL), organics were washed with water (10 mL), brine (2×10 mL) and dried over Na2SO4 and concentrated. The residue was used to the next step without further purification.

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