Imidazole → HCID 18536138, compound

HRID 412184Notes

Reaction equation

HRID 412184 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[I:1])=[CH:7][CH:8]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 6229868-Iodo-2-naphthol

Product 1

HCID 18536138HCID 18536138, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-iodo-2-naphthol, as described in Step A of Example 103 (2.75 g, 10.2 mmol) in dry DMF (25 mL), under argon, were added imidazole (1.39 g, 20.4 mmol) and triisopropylsilyl chloride (2.55 g, 13.2 mmol). The resulting mixture was stirred at ambient temperature for 4 hrs, then quenched with 10% aqueous citric acid (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water (50 mL), then brine (50 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with CH2Cl2—50% hexane to yield the desired product as a white solid.

Workup

  1. customquenched with 10% aqueous citric acid (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic extracts were washed with water (50 mL)
  4. dry with materialbrine (50 mL), then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with CH2Cl2—50% hexane

Sources & evidence

ORD record
ord-ba6268baaacd42cc88dfad742fc756e4
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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