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
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
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.
Workup
- temperatureto warm to room temperature
- stirringstirred for 1.5 h
- customThe reaction mixture was quenched with saturated NH4Cl solution
- extractionextracted with EtOAc (3×5 mL)
- washorganics were washed with water (10 mL), brine (2×10 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was used to the next step without further purification
Sources & evidence
- ORD record
- ord-c12b5c5f33cf4777a126859380a054a3
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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