Sodium hydride → 3-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-ylmethyl]-benzonitrile

HRID 230427

반응식

HRID 230427 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:42]=[CH:41][CH:40]=[C:39]([C:43]#[N:44])[CH:38]=1.[NH4+].[Cl-]>CN(C=O)C>[Cl:29][C:28]1[C:20]([Cl:19])=[CH:21][C:22]2[N:9]([CH2:36][C:37]3[CH:38]=[C:39]([CH:40]=[CH:41][CH:42]=3)[C:43]#[N:44])[C:24]([CH2:30][C:31]([F:32])([F:33])[F:34])=[N:25][C:26]=2[CH:27]=1

참가 물질

7

반응물 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 669688335,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-1H-indoleHCID 66968977dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

생성물 1

HCID 444302053-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-ylmethyl]-benzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

NaH (60%) (60 mg, 1.5 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 (269 mg, 1 mmol) in DMF (5 ml) at 0° C. The resulting mixture was stirred at 0° C. for half hour. α-bromo-m-tolunitrile (294 mg, 1.5 mmol) was 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-3dd0c9d6c76c4aa695e66e4c93d9d1e5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566733B2

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