Sodium Carbonate → Methyl 3-amino-4-[5-cyano-2-(ethoxymethyl)-3-(2-hydroxy-2-methylpropyl)-1H-imidazol-4-yl]benzoate

Participants

Reaction Conditions

Reaction Steps

In an inert atmosphere 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-5-iodo-1H-imidazole-4-carbonitrile (3.66 g, 10.5 mmol) was combined with dimethoxyethane (43 mL) to give a light brown solution. To this solution were added Pd(OAc)2 (118 mg, 524 μmol), triphenylphosphine (275 mg, 1.05 mmol) and methyl 3-amino-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (4.36 g, 15.7 mmol) with stirring. Finally Na2CO3 (2 M, 15.7 mL, 31.4 mmol) was added. The reaction mixture was heated to 100° C. and stirred for 1 hour. After cooling to room temperature the mixture was partitioned between ethyl acetate (70 mL, 2×50 mL) and water (70 mL). The organic phases were combined, dried over MgSO4, concentrated in vacuo and purified by flash chromatography (silica gel, 0% to 100% ethyl acetate in heptane) to give the title compound (2.79 g, 71%) as light brown foam that was used in the next step without further purification.

Provenance & Evidence