Imidazole → 6-Bromo-2-(tert-butyldimethylsilyloxy)-N-methyl-1-naphthamide

HRID 480453Notes

Reaction equation

HRID 480453 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([OH:16])[CH:6]=[CH:5]2.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 187690866-Bromo-2-hydroxy-N-methyl-1-naphthamide

Product 1

HCID 187691556-Bromo-2-(tert-butyldimethylsilyloxy)-N-methyl-1-naphthamideYield 94.6%

Procedure

A mixture of 6-bromo-2-hydroxy-N-methyl-1-naphthamide (2.50 g), tert-butyldimethylsilyl chloride (1.61 g), and imidazole (912 mg) in DMP (30 mL) was stirred for 2 h at room temperature. After dilution with water, the resulting mixture was extracted with AcOEt. The organic layer was washed with water and brine followed by concentrating in vacuo. The residue was passed through silica gel plug (hexane:AcOEt=1:1). The elute was concentrated, and the residue was washed with hexane to give the titled compound (3.33 g) as colorless needles.

Workup

  1. extractionAfter dilution with water, the resulting mixture was extracted with AcOEt
  2. washThe organic layer was washed with water and brine
  3. concentrationby concentrating in vacuo
  4. concentrationThe elute was concentrated
  5. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-1397b2e52e114acaaeff57aac996458b
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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