2-tert-Butyl-1-methyl-4-(trimethylstannyl)-1H-imidazole synthesis

Yield:936718-20-6 82%

Reaction Conditions:

Stage #1: 1-methyl-4-iodo-2-tert-butylimidazolewith ethylmagnesium bromide in diethyl ether;dichloromethane at 20; for 1 h;
Stage #2: trimethyltin(IV)chloride in diethyl ether;dichloromethane at 20; for 16.0833 h;

Steps:

5

To a stirred solution of 2-t-butyl-4-iodo-l -methyl- lH-imidazole (8.0 g, 30.3 mMol) in Cη2CI2 (80 mL) was added dropwise at RT under N2 a solution of 3.0 M EtMgBr in Et2θ ( 12 mL, 36 mMol). After stirring for 1 h, a solution of 1.0 N trimethyltin chloride inTHF (32 mL, 32 mMol) was added dropwise over 5 minutes. The reaction was stirred at RT for 16 h, concentrated under vacuum, taken up in EtOAc, washed with aq. NH4CI, dried(MgSO/].), filtered and evaporated under vacuum. Short path distillation under vacuum (0.2 mmHg, 1 10- 120 ⁰C) gave the title compound (7.49 g, 82%) as a clear oil which solidified to a waxy solid in the refrigerator: ¹H NMR (400 MHz, CDCl₃) J 6.81 (s, 1 H), 3.78 (s, 3 H), 1.48 (s, 9 H), 0.32 (s, 9 H).

References:

WO2007/56143,2007,A2 Location in patent:Page/Page column 62