Cesium carbonate → 7-Bromo-1-(4-trifluoromethylbenzyl)-1,3-dihydro-indol-2-one
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=O.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1>CN(C=O)C.CCCCCC.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=1)[C:8](=[O:11])[CH2:7]2Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
A mixture of 7-bromo-1H-indole-2,3-dione (4.5 g), Cs2CO3 (10 g) and 1-bromomethyl-4-trifluoromethylbenzene (5 g) in 50 ml of DMF was stirred at 55° C. for 6 h. The reaction mixture was cooled to r.t., diluted with 100 ml of 1:1 hexane/EtOAc and filtered through a pad of silica gel. The filtrate was concentrated under vacuum and the crude product was dissolved in 100 ml of ethanol and 10 ml of 50% aqueous solution of hydrazine. The resulting mixture was heated to reflux for 10 h and diluted with 50 ml of water. After cooling to r.t., solid was collected by filtration and air-dried to give the title compound as a white solid (5.2 g).
Workup
- temperatureThe reaction mixture was cooled to r.t.
- filtrationfiltered through a pad of silica gel
- concentrationThe filtrate was concentrated under vacuum
- dissolutionthe crude product was dissolved in 100 ml of ethanol
- temperatureThe resulting mixture was heated
- temperatureto reflux for 10 h
- additiondiluted with 50 ml of water
- temperatureAfter cooling to r.t.
- filtrationsolid was collected by filtration
- customair-dried
Sources & evidence
- ORD record
- ord-4f8b0e1e06c0456690b2d1daa03a89eb
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404736B2
Reaction notes
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