Tributyltin Chloride → 4-Cyclopropylmethoxy-2-tributylstannanyl-pyridine
Reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)[CH:5]=[CH:4][N:3]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH:10]1([CH2:9][O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])[CH:7]=2)[CH2:12][CH2:11]1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
In a round bottomed flask 2-bromo-4-cyclopropylmethoxy-pyridine (315 mg, 1.38 mmol) was dissolved in THF (6 mL). The solution was cooled to 0° C. and isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 1.1 mL, 1.45 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min then at room temperature for 1.5 h. Tributyltin chloride (0.42 mL, 1.52 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and concentrated to give 4-cyclopropylmethoxy-2-tributylstannanyl-pyridine as a yellow oil which was used without further purification.
Workup
- waitat room temperature for 1.5 h
- stirringthe reaction mixture was stirred at room temperature for 2 h
- customThe reaction mixture was quenched with water
- extractionextracted with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-600960ef5b304b2e8efa5806602449aa
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518945B2
Reaction notes
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