Butyl iodide → HCID 22497248, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O>[CH2:24]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7]1)[CH2:25][CH2:26][CH3:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (200 mg, 0.81 mmol) and potassium carbonate (214 mg, 2.02 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 25° C. for 30 min. The reaction was then treated with 1-iodobutane (0.14 mL, 1.21 mmol) and heated at 60° C. for 5 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL) and was washed with a saturated aqueous sodium bicarbonate solution (1×50 mL), water (2×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-(1-butyl-6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (283.7 mg) as an orange oil which was used without further purification or characterization.
Workup
- temperatureheated at 60° C. for 5 h
- temperatureAt this time, the reaction was cooled to 25° C.
- concentrationconcentrated in vacuo
- additionThe residue was diluted with ethyl acetate (50 mL)
- washwas washed with a saturated aqueous sodium bicarbonate solution (1×50 mL), water (2×50 mL)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-364e293f1b354d51a39bb6651e8726f4
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881844B2
Reaction notes
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