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

HRID 13270
Notes
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Reaction equation

HRID 13270 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f469e0a278614344920035b41353c220
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes