Tributyltin Chloride → HCID 57516633, compound
Reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[CH2:18]([Sn:22]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])Cl)[CH2:19][CH2:20][CH3:21]>C1COCC1>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Sn:22]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -16 °C
Procedure
In a round-bottomed flask, 2-iodo-4-thiophen-2-yl-pyridine (150 mg, 0.52 mmol) was dissolved in THF (3.2 mL). The light yellow solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0M solution in THF, 0.30 mL, 0.60 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.17 mL, 0.63 mmol) was slowly added. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched with saturated NH4Cl solution and then extracted with 50 mL EtOAc (2×). The combined organic layers were washed with 5 mL water and once with 5 mL brine then dried over sodium sulfate, filtered and concentrated to afford 4-thiophen-2-yl-2-(tributylstannanyl)pyridine a light brown oil which was used without further purification.
Workup
- additionwas added dropwise
- additionAfter the addition
- temperatureto warm to room temperature
- stirringstirred for 1 h
- customThe reaction mixture was quenched with saturated NH4Cl solution
- extractionextracted with 50 mL EtOAc (2×)
- washThe combined organic layers were washed with 5 mL water and once with 5 mL brine
- dry with materialthen dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3c541d988edb47deb5e1684b085e63f5
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518945B2
Reaction notes
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