Imidazole → HCID 18433609, compound

HRID 2306196Notes

Reaction equation

HRID 2306196 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[C:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:4][CH:3]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:9][CH:10]=2)[C:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18433560HCID 18433560, compound

Product 1

HCID 18433609HCID 18433609, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-1-tert-butoxycarbonylaminonaphth-7-ol, as described above in Step C, (1.62 g, 4.80 mmol), tert-butyldimethylsilyl chloride (1.09 g, 7.20 mmol), and imidazole (0.82 g, 12 mmol), was stirred in dry DMF (40 mL) at ambient temperature for 18 hours. The solvent was removed under reduced pressure, and the residue was partitioned between H2O (100 mL) and Et2O (200 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with CH2Cl2—50% hexane to yield the desired product as a pale solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between H2O (100 mL) and Et2O (200 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica
  8. washeluting with CH2Cl2—50% hexane

Sources & evidence

ORD record
ord-6ab23e951f04435286d927f473e45496
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

Loading…