Tetrabutylammonium Fluoride → HCID 68591664, compound

HRID 1512186Notes

Reaction equation

HRID 1512186 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35]([NH:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([N:48]3[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]3)[CH:39]=1)=[O:36])=[CH:30][CH:29]=[CH:28]2)(C)C>O1CCCC1>[OH:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35]([NH:37][C:38]1[CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:41]=[C:40]([N:48]3[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]3)[CH:39]=1)=[O:36])=[CH:30][CH:29]=[CH:28]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 685910626[[(1,1-dimethylethyl)diphenylsilyl]oxy]-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide

Product 1

HCID 68591664HCID 68591664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride (3.5 mL of 1 M) in tetrahydrofuran is added to a stirred solution of 6[[(1,1-dimethylethyl)diphenylsilyl]oxy]-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide (1.91 g, 2.94 mmol) in tetrahydrofuran (50 mL) and the mixture is stirred at room temperature for 60 min. The solvent is evaporated off under reduced pressure and the residue is purified by column chromatography (SiO2; ethyl acetate) to afford the title compound as a cream solid m.p.: 169-172° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customthe residue is purified by column chromatography (SiO2; ethyl acetate)

Sources & evidence

ORD record
ord-9f1efda01bd0496ba66bb5258043ba3e
Source dataset
uspto-grants-2012_07
Patent number
US08217045B2

Reaction notes

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