18-Crown-6 → 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-[hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile

HRID 1594874Notes

Reaction equation

HRID 1594874 reaction equation
F[C:2]1[CH:9]=[C:8]([CH:10]([OH:17])[C:11]2[N:12]([CH3:16])[CH:13]=[N:14][CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:18]([C:20]1([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)[CH2:26][CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[C:21]1=[O:28])[CH3:19].[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[CH2:18]([C:20]1([C:29]2[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=2)[O:35][C:2]2[CH:9]=[C:8]([CH:10]([OH:17])[C:11]3[N:12]([CH3:16])[CH:13]=[N:14][CH:15]=3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:26][CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[C:21]1=[O:28])[CH3:19]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 27945733-Ethylhexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-oneHCID 185332012-Fluoro-4-(hydroxy(1-methyl-1h-imidazol-5-yl)methyl)benzonitrile

Product 1

HCID 111025492-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-[hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-4-[hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile (as described in Step E above) (0.162 g, 0.700 mmol), 3-ethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one (0.173 g, 0.700 mmol) and KF.Al2O3 (0.208 g) and 18-Crown-6 (0.017 g, 0.064 mmol) were dissolved in anhydrous CH3CN (7 mL) and refluxed under Ar for 24 h. The reaction was filtered, concentrated and purified using SiO2 chromatography (1-3% MeOH/CH2Cl2).

Workup

  1. temperaturerefluxed under Ar for 24 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-56b1a4c3c7a54617951a3fd4ca881a31
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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