Tetrabutylammonium Fluoride → HCID 136407108, compound

HRID 1479933Notes

Reaction equation

HRID 1479933 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C:27]1[CH:28]=[CH:29][C:30]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[N:47]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:46]4[CH:54]=[CH:55][CH:56]=[CH:57][C:45]=4[N:44]=3)=[CH:39][CH:38]=2)=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)(C(C)(C)C)(C)C>C1COCC1>[C:48]1([N:47]2[C:46]3[CH:54]=[CH:55][CH:56]=[CH:57][C:45]=3[N:44]=[C:43]2[C:40]2[CH:39]=[CH:38][C:37]([C:30]3[CH:29]=[CH:28][C:27]([OH:26])=[C:36]4[C:31]=3[CH:32]=[CH:33][CH:34]=[N:35]4)=[CH:42][CH:41]=2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67362201HCID 67362201, compound

Product 1

HCID 136407108HCID 136407108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M TBAF solution in THF (22.4 ml, 22.4 mmol) is added dropwise to a solution of 8-(tert-butyldimethylsilanyloxy)-5-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]quinoline (7.9 g, 14.90 mmol) in THF (20 ml). After stirring for 4 h, the mixture is washed with 5% aqueous NH4Cl (100 ml) solution and extracted with ethyl acetate (3×50 ml). The combined organic phases are dried over sodium sulfate, and the solvent is removed under reduced pressure. The crude product is purified by flash chromatography on silica and crystallisation from MeOH (5.9 g, 90%).

Workup

  1. washthe mixture is washed with 5% aqueous NH4Cl (100 ml) solution
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe crude product is purified by flash chromatography on silica and crystallisation from MeOH (5.9 g, 90%)

Sources & evidence

ORD record
ord-d6c024d8e15c48339353664821fc5e92
Source dataset
uspto-grants-2016_08
Patent number
US09409883B2

Reaction notes

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