Potassium Iodide → 4-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-ylmethyl]-benzoic acid ethyl ester
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[CH2:36][C:37]1[CH:47]=[CH:46][C:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:39][CH:38]=1.[I-].[K+].[NH4+].[Cl-]>CN(C=O)C>[CH2:44]([O:43][C:41](=[O:42])[C:40]1[CH:46]=[CH:47][C:37]([CH2:36][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:39]=1)[CH3:45]Participants
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. Ethyl 4-(bromomethyl)-benzoate (729.3 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 extracted with EtOAc. The organic layer was washed with brine, then dried over anhydrous MgSO4. The solvent was distilled out under reduced pressure. Column chromatography (silica gel, EtOAc/hexanes (0% to 60%) yielded the title compound as an off-white solid.
Workup
- customat 0° C
- temperatureThe reaction temperature was raised to 25° C.
- stirringthe reaction mixture was stirred for 18 hours
- extractionextracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous MgSO4
- distillationThe solvent was distilled out under reduced pressure
Sources & evidence
- ORD record
- ord-e288c591cd2140dbb1551511797168ce
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586616B2
Reaction notes
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