Tributyltin Chloride → 5,6-dichloro-1-methyl-3-tributylstannanyl-1H-indazole
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([CH3:12])[N:6]=[C:5]2I.C([Mg]Cl)(C)C.[CH2:19]([Sn:23]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])Cl)[CH2:20][CH2:21][CH3:22]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([CH3:12])[N:6]=[C:5]2[Sn:23]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:19][CH2:20][CH2:21][CH3:22]Participants
5
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 5,6-dichloro-3-iodo-1-methyl-1H-indazole (150 mg, 0.44 mmol) in THF (3 mL) at −10° C. (ice/acetone) was slowly added isopropylmagnesium chloride (2.0 M in THF, 0.26 mL, 0.52 mmol). The bright yellow heterogeneous reaction mixture was stirred at −10° C. for 15 min then tributylchlorostannane (0.14 mL, 0.52 mmol) was added dropwise. Stirring was continued at −10° C. for 30 min then at room temperature for 1 h. The reaction mixture was quenched with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated to afford 5,6-dichloro-1-methyl-3-tributylstannanyl-1H-indazole as a pale yellow oil which was used in the next step without further purification.
Workup
- customat −10° C.
- stirringStirring
- waitwas continued at −10° C. for 30 min
- waitat room temperature for 1 h
- customThe reaction mixture was quenched with water
- extractionextracted with EtOAc (2×)
- dry with materialThe combined organics were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e37eac3152f04b6f9efcefaa2c52da73
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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