Tributyltin Chloride → 1-Methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile
Reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[N:4]([CH3:13])[N:3]=1.IC1C2C(=CC(C#N)=CC=2)NN1C.C([Mg]Cl)(C)C.Cl[Sn:33]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37]>C1COCC1>[CH3:13][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[C:2]([Sn:33]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:34][CH2:35][CH2:36][CH3:37])=[N:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
A mixture 3-iodo-1-methyl-1H-indazole-6-carbonitrile and 3-iodo-2-methyl-1H-indazole-6-carbonitrile (160 mg, 0.565 mmol) was dissolved in THF (6 mL). The solution was cooled to −40° C. Isopropylmagnesium chloride 2M in THF (0.34 mL, 0.678 mmol) was added drop-wise at −40° C. The reaction mixture was stirred at −40° C. for 20 min, then chlorotributyltin (0.18 mL, 0.678 mmol) 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 (3×10 mL), combined organics were washed with water (10 mL), brine (10 mL), dried over Na2SO4 and concentrated. The residue was used in the next step without further treatment.
Workup
- temperatureto warm to room temperature
- stirringstirred for 1.5 h
- customThe reaction mixture was quenched with saturated NH4Cl solution
- extractionextracted with EtOAc (3×10 mL)
- washcombined organics were washed with water (10 mL), brine (10 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ce38cc997e1b4fd0b4b5f63bd71ae258
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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