Imidazole → HCID 12129258, compound

HRID 2090305Notes

Reaction equation

HRID 2090305 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CN(C)C=O.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>>[Si:22]([O:11][C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N:1]2)=[CH:6][CH:7]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1354268667-Hydroxyquinoline

Product 1

HCID 12129258HCID 12129258, compound

Procedure

At room temperature to a solution of quinolin-7-ol (Matrix Scientific, Cat. No. 007603; 0.6 g, 4 mmol) in N,N-Dimethylformamide (10 mL, 100 mmol) was added 1H-imidazole (0.670 g, 9.84 mmol), followed by tert-butyldimethylsilyl chloride (0.934 g, 6.20 mmol) with stirring. The mixture was stirred at room temperature overnight, then quenched with sat'd NaHCO3 solution, and extracted with methylene chloride (3×). The combined extracts were washed with water and brine successively, and then dried over Na2SO4. After filtration, the filtrate was concentrated and purified with flash column using 15% ethyl acetate in hexane as eluent to yield 0.88 g of the product. LCMS (M+H)+: m/z=260.3.

Workup

  1. customAt room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. customquenched with sat'd NaHCO3 solution
  4. extractionextracted with methylene chloride (3×)
  5. washThe combined extracts were washed with water and brine successively
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. custompurified with flash column

Sources & evidence

ORD record
ord-957addf9b06c492f8135c0f562d657e1
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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