Sodium hydride → 2-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-yl]-1-(5-methyl-3-phenyl-isoxazol-4-yl)-ethanone

HRID 230429

반응식

HRID 230429 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]([C:39]1[C:40]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[N:41][O:42][C:43]=1[CH3:44])=[O:38].[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]([C:39]3[C:40]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[N:41][O:42][C:43]=3[CH3:44])=[O:38])[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 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazoleHCID 669688335,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-1H-indoleHCID 66968977dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

생성물 1

HCID 596822962-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-yl]-1-(5-methyl-3-phenyl-isoxazol-4-yl)-ethanone

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 hours. 2-bromo-1-(5-methyl-3-phenylisoxazol-4-yl)ethan-1-one (420 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 a 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-ffff62f7bc4a4bfda5129fdd0db1be83
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566733B2

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