Imidazole → HCID 18433490, compound

HRID 2306273Notes

Reaction equation

HRID 2306273 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1.O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:7][CH:8]=2)[C:3]=1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 18433604HCID 18433604, compound

Product 1

HCID 18433490HCID 18433490, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-1-(tert-butoxycarbonylamino)-7-hydroxynaphthalene, as described above in Step F, (4.80 g, 14.19 mmol), tert-butyldimethylsilyl chloride (2.8 g, 18.45 mmol) and imidazole (2.2 g, 32.64 mmol) were dissolved in DMF (25 mL) and stirred for 18 hours. The mixture was poured into H2O and extracted with Et2O (2×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with CH2Cl2—50% hexanes, to yield the above-titled compound.

Workup

  1. extractionextracted with Et2O (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with CH2Cl2—50% hexanes

Sources & evidence

ORD record
ord-f15e0268801b41acb88a011b48cd8805
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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