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

HRID 1394514노트

반응식

HRID 1394514 반응식
[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]

참가 물질

8

반응물 6

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 669688335,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-1H-indoleHCID 66968977dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

생성물 1

HCID 444302014-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-ylmethyl]-benzoic acid ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  1. customat 0° C
  2. temperatureThe reaction temperature was raised to 25° C.
  3. stirringthe reaction mixture was stirred for 18 hours
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. distillationThe solvent was distilled out under reduced pressure

출처 및 근거

ORD 기록
ord-362f873ee6d74546a5516f3a252a01d7
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348438B2

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