4-Fluorobenzonitrile → 4-(6-(1-acetyl-pyrrolidin-2-yl)-2-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-5-yloxy)-benzonitrile

HRID 13270

반응식

HRID 13270 반응식
[H-].[Na+].[OH:3][C:4]1[C:5]([CH:27]2[CH2:31][CH2:30][CH2:29][N:28]2[C:32](=[O:34])[CH3:33])=[CH:6][C:7]2[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:9][C:8]=2[CH:26]=1.F[C:36]1[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[C:32]([N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[C:5]1[C:4]([O:3][C:36]2[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=2)=[CH:26][C:8]2[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=2[CH:6]=1)(=[O:34])[CH3:33]

참가 물질

6

반응물 4

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 231452771-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

생성물 1

HCID 231458334-(6-(1-acetyl-pyrrolidin-2-yl)-2-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-5-yloxy)-benzonitrile

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

5.8 mg of sodium hydride was added to an N-methyl-pyrrolidinone (1 ml) solution of 30 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone obtained in Example 121 (step 10) and 20 mg of 4-fluorocyanobenzene, and the reaction liquid was stirred overnight in a sealed tube at 100° C. After cooled, aqueous saturated sodium bicarbonate was added to the reaction liquid, then this was extracted with ethyl acetate, the organic layer was washed with water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as a yellow oily substance.

후처리

  1. customthe reaction liquid
  2. temperatureAfter cooled
  3. extractionthis was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified
  8. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)
  9. customto obtain the entitled compound as a yellow oily substance

출처 및 근거

ORD 기록
ord-f469e0a278614344920035b41353c220
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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