Potassium Iodide → HCID 16721132, compound
Reaction equation
[H-].[Na+].ClC1C2N=C(CC(F)(F)F)[N:9](Cl)C=2C=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[Cl:29])[NH:25][C:24]([CH2:30][C:31]([F:34])([F:33])[F:32])=C2.[Br:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1.[I-].[K+].[NH4+].[Cl-]>CN(C=O)C>[Br:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][N:9]2[C:22]3[CH:21]=[C:20]([Cl:19])[C:28]([Cl:29])=[CH:27][C:26]=3[N:25]=[C:24]2[CH2:30][C:31]([F:32])([F:33])[F:34])=[CH:38][CH:37]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
NaH (60%) 120 mg, 3 mmol) was added into a solution of dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole. 5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-1H-indole (538 mg, 2 mmol) in DMF (5 ml) at 0° C. The resulting mixture was stirred at 0° C. for half hour. 4-bromo-benzyl bromide (749.8 mg, 3 mmol) and potassium iodide (498 mg, 3 mmol) were then added to the reaction mixture at 0° C. The reaction temperature was raised to 25° C. and then the reaction mixture was stirred for 18 hours. NH4Cl (aq.) was added and then the reaction mixture was extracted with EtOAc. The organic layer was washed with brine, then dried over anhydrous MgSO4. Solvent was distilled out under reduced pressure. Column chromatography (silica gel, EtOAc/hexanes (0% to 60%) yielded the title compound as a solid light brown solid.
Workup
- customat 0° C
- temperatureThe reaction temperature was raised to 25° C.
- stirringthe reaction mixture was stirred for 18 hours
- extractionthe reaction mixture was extracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous MgSO4
- distillationSolvent was distilled out under reduced pressure
Sources & evidence
- ORD record
- ord-e08b0bb48f0e49e1bac1f90bb9b9073f
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348438B2
Reaction notes
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