Potassium Iodide → 4-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-ylmethyl]-benzoic acid ethyl ester

HRID 230444

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

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-25dfd7e982a0466991a479152e3407db
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566733B2

Linked notes

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