Reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[N:8]=[C:7]2I.C([Mg]Cl)(C)C.[CH2:21]([Sn:25]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])Cl)[CH2:22][CH2:23][CH3:24]>C1COCC1>[F:1][CH:2]([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[N:8]=[C:7]2[Sn:25]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH3:24]Participants
5
Conditions
- Temperature
- -16 °C
Procedure
5-(Difluoromethoxy)-3-iodo-1-methyl-1H-indazole (0.265 g, 818 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, 458 μL, 916 μmol) added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (306 mg, 255 μL, 940 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), organics dried over MgSO4 and concentrated to a yellow oil. The residue was dried under high vacuum and taken into 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 materialorganics dried over MgSO4
- concentrationconcentrated to a yellow oil
- customThe residue was dried under high vacuum
- customtaken into next step without further purification
Sources & evidence
- ORD record
- ord-ade00f536a8e4f59869b3e4da9cb8039
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Linked notes
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