Tributyltin Chloride → 4-tributylstannanyl-1-(2,3,5-trifluoro-phenyl)-1H-imidazole
Reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[C:8]=2[F:15])[CH:6]=1.C([Mg]Cl)(C)C.[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24].[NH4+].[Cl-]>C1COCC1>[CH2:30]([Sn:25]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:26][CH2:27][CH2:28][CH3:29])[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[C:8]=2[F:15])[CH:6]=1)[CH2:31][CH2:32][CH3:33]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-iodo-1-(2,3,5-trifluorophenyl)-1H-imidazole (0.140 g, 0.43 mmol) in 2 mL of THF under Ar was chilled in an ice/water bath 5 min. Isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 0.225 mL, 0.45 mmol) was added, the bath was removed, and the pale yellow solution was stirred for 1.5 h. Tributyltin chloride (0.055 mL, 0.20 mmol) was added all at once, and the pale yellow solution was stirred 1 h. A sat. aq. NH4Cl solution (10 mL) was added, and the mixture was extracted with two 10 mL portions of EtOAc. The combined organic layers were washed with 10 mL of a sat. aq. NaCl solution, dried over Na2SO4, filtered and concentrated to give 4-tributylstannanyl-1-(2,3,5-trifluoro-phenyl)-1H-imidazole as a yellow oil which was used without further purification.
Workup
- customthe bath was removed
- stirringwas stirred 1 h
- extractionthe mixture was extracted with two 10 mL portions of EtOAc
- washThe combined organic layers were washed with 10 mL of a sat. aq. NaCl solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4d86e693c3334ad7bcc2806afed3319a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518945B2
Reaction notes
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