Potassium bis(trimethylsilyl)amide → HCID 86619474, compound
Reaction equation
[C:1]([C:5]1[O:6][C:7]([C:10]2[C:14]([CH:15]=[C:16](Br)Br)=[C:13]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])[N:11]=2)=[N:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>O1CCCC1>[C:1]([C:5]1[O:6][C:7]([C:10]2[C:14]([C:15]#[CH:16])=[C:13]([C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[N:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=3[Cl:33])[N:11]=2)=[N:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 78 °C
Procedure
To a solution of 2-tert-butyl-5-(5-(4-chlorophenyl)-4-(2,2-dibromovinyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole (230 mg, 0.36 mmol) in tetrahydrofuran (10 ml) at 78° C., potassium bis(trimethysilyl)amide (1.46 ml, 0.5 M solution in tetahydrofuran, 0.73 mmol) was added slowly. After stirring for 20 minutes at 78° C., the resulting solution was quenched with saturated ammonium chloride (5 ml). After warming up to room temperature, the solution was diluted with ethyl ether, and then the organic layer was extracted with ethyl acetate (50 ml twice). After evaporation, crude residue was purified with silica gel column (hexane/ethyl acetate=5/1) to obtain title compound (150 mg, 91% yield) as light yellow solid.
Workup
- customthe resulting solution was quenched with saturated ammonium chloride (5 ml)
- temperatureAfter warming up to room temperature
- additionthe solution was diluted with ethyl ether
- extractionthe organic layer was extracted with ethyl acetate (50 ml twice)
- customAfter evaporation, crude residue
- customwas purified with silica gel column (hexane/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-4153e5677b3541a98906c7a439d1afb6
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875647B2
Reaction notes
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