Sodium Bicarbonate → 5-tert-butyl-N-{3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenyl}-2-methoxy-benzamide

Participants

Reaction Steps

3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenylamine (Example 3) (80 mg, 0.23 mmol) was dissolved in THF (5 mL) under N2 and 0.9 mL of 1 M LiHMDS (0.9 mmol) was slowly added. After stirring for 5 min, a solution of 51.8 mg (0.23 mmol) of 5-tert-butyl-2-methoxy-benzoic acid methyl ester in 5 mL of THF was added. The mixture was stirred at for 45 min, then saturated NaHCO3 (10 mL) was slowly added. The resulting mixture was then extracted with CH2Cl2 (100 mL). Chromatography (30 to 100% EtOAc in hexanes) provided the title compound as a tan foam (62 mg, 50%). ESI MS m/z 534 [C33H35N5O2+H]+.

Provenance & Evidence