Imidazole → HCID 67345597, compound

HRID 882086Notes

Reaction equation

HRID 882086 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:15]#[N:16])[C:11]=1[N:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH2:17][OH:18])[CH:6]=[CH:5]2.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:15]#[N:16])[C:11]=1[N:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH2:17][O:18][Si:23]([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67324605HCID 67324605, compound

Product 1

HCID 67345597HCID 67345597, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 6-bromo-7-dimethylamino-2-(hydroxymethyl)quinoline-8-carbonitrile (2 g, 6.5 mmol, 1 eq), TBDMSCl (1.4 g, 7.3 mmol, 1.1 eq) and imidazole (623 mg, 7.3 mmol, 1.1 eq) were added to DMF (20 mL). The resulting solution was stirred at room temperature for 3 hours, and then the solvent was removed under high reduced pressure. Cyclohexane was added and the mixture was washed twice with water, and then with brine. The organic layer was then dried over MgSO4, and concentrated under reduced pressure. The product was obtained pure as a yellow powder (1.9 g, 68%).

Workup

  1. customthe solvent was removed under high reduced pressure
  2. additionCyclohexane was added
  3. washthe mixture was washed twice with water
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-185d4300115d4f52b89b0b70901554fa
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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