(4-BroMo-iMidazol-1-yl)-acetic acid tert-butyl ester synthesis

Yield: 79%

Reaction Conditions:

with potassium hydroxide;potassium carbonate;tetra-n-butyl ammonium bromide in dichloromethane

Steps:

46
General Procedure 46 To a mixture of 4-bromo-imidazole (995 mg, 6.77 mmol), potassium hydroxide (380 mg, 6.77 mmol), potassium carbonate (936 mg, 6.77 mmol) and tetra-n-butyl ammonium bromide (109 mg, 0.339 mmol) in dichloromethane (7 mL) was added tert-butyl bromo acetate (0.50 mL, 3.4 mmol). After stirring overnight the reaction was filtered. The filtrate was dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, ethyl acetate to afford (4-Bromo-imidazol-1-yl)-acetic acid tert-butyl ester (696 mg, 79%).

References:

AGOURON PHARMACEUTICALS, INC. US2006/46991, 2006, A1 Location in patent:Page/Page column 49