Imidazole → HCID 58585766, compound

HRID 1297679Notes

Reaction equation

HRID 1297679 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:16])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:17]#[N:18].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C>[C:27]([Si:24]([CH3:26])([CH3:25])[O:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:16])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:17]#[N:18])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58585824HCID 58585824, compound

Product 1

HCID 58585766HCID 58585766, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the solution of 4-(3-hydroxy-propylsulfanyl)-6-iodo-quinoline-3-carbonitrile (example 50a, 3.0 g, 8.1 mmol) and imidazole (2.2 g, 32.4 mmol) in DMF (10 mL) was added dropwisely the solution of tert-butyldimethylsilyl chloride (TBDMS-Cl, 2.94 g, 19.4 mmol) in DMF (10 mL). The reaction mixture was stirred at room temperature overnight. The product was extracted with ethylacetate. The combined organic layers were successively washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 5%-30% ethyl acetate in hexanes in 50 min) afforded 4-[3-(tert-butyl-dimethyl-silanyloxy)-propylsulfanyl]-6-iodo-quinoline-3-carbonitrile (3.41 g, 87%) as a yellow solid. LC-MS m/e 485 (MH+).

Workup

  1. extractionThe product was extracted with ethylacetate
  2. washThe combined organic layers were successively washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09f11720b9394b958c0e07d1abfc63f5
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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