Imidazole → HCID 67345597, compound

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

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%).