Tributyltin Chloride → 1-Methyl-3-(tributylstannyl)-5-(trifluoromethoxy)-1H-indazole
Reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]([F:15])([F:14])[F:13])[CH:9]=2)[N:4]([CH3:16])[N:3]=1.C([Mg]Cl)(C)C.[CH2:22]([Sn:26]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])Cl)[CH2:23][CH2:24][CH3:25]>C1COCC1>[CH3:16][N:4]1[C:5]2[C:10](=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=2)[C:2]([Sn:26]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:3]1Participants
5
Conditions
- Temperature
- -16 °C
Procedure
3-Iodo-1-methyl-5-(trifluoromethoxy)-1H-indazole (0.141 g, 412 μmol) was dissolved in THF (3.00 mL). The colorless solution was cooled to −16° C. (NaCl/ice bath), then isopropylmagnesium chloride 2M in THF (231 μL, 462 μmol) was added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min. Tributylchlorostannane (154 mg, 129 μL, 474 μmol) was added slowly. The reaction mixture was warmed to 25° C. and stirred for 1.5 h. The reaction mixture was quenched with saturated ammonium chloride solution, extracted with dichloromethane (3×30 mL), the organics dried over MgSO4 and concentrated to a yellow oil. The residue was dried under high vacuum and taken into the next step without further purification.
Workup
- temperatureThe reaction mixture was warmed to 25° C.
- stirringstirred for 1.5 h
- customThe reaction mixture was quenched with saturated ammonium chloride solution
- extractionextracted with dichloromethane (3×30 mL)
- dry with materialthe organics dried over MgSO4
- concentrationconcentrated to a yellow oil
- customThe residue was dried under high vacuum
- customtaken into the next step without further purification
Sources & evidence
- ORD record
- ord-01727a7607d246d7a6cb8be6e88d7811
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
Loading…