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

HRID 230428

反応式

[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[C:38]([C:43]#[N:44])=[CH:39][CH:40]=[CH:41][CH:42]=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:42]=[CH:41][CH:40]=[CH:39][C:38]=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

参加物

反応条件

温度: 0 °C

実験手順

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-o-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.

後処理

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

出典と根拠

ORDレコード: ord-f3a638c8105d446fb99b973a2ad38dee
出典データセット: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07566733B2

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート