Potassium Iodide → 1-(2-Bromo-benzyl)-5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

HRID 230445

反応式

HRID 230445 の反応式
[H-].[Na+].Cl[C:4]1[C:12]2N=C(CC(F)(F)F)N(Cl)[C:8]=2[CH:7]=[CH:6][CH:5]=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]CC1C=CC(C(OCC)=O)=CC=1.[I-].[K+].[NH4+].[Cl-].C[N:53]([CH:55]=O)C>>[Br:35][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:12]=1[CH2:55][N:53]1[C:22]2[CH:21]=[C:20]([Cl:19])[C:28]([Cl:29])=[CH:27][C:26]=2[N:25]=[C:24]1[CH2:30][C:31]([F:32])([F:33])[F:34]

参加物

8

反応物 7

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 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

生成物 1

HCID 444301391-(2-Bromo-benzyl)-5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

反応条件

温度
0 °C

実験手順

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 a white solid.

後処理

  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

出典と根拠

ORDレコード
ord-2416a624f1ad42318eada988864f5255
出典データセット
uspto-grants-2009_07
特許番号
US07566733B2

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