Water → 3,5-Dimethoxy-4-methyl-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-phenylamino-benzyl]-benzamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of Pd(P(t-Bu3)2 (3.3 mg, 0.0065 mmol) and cetyltrimethylammonium bromide (1.2 mg, 0.0033 mmol) in toluene (2 mL) was added compound 1g (250 mg, 0.65 mmol), bromobenzene (0.072 mL, 0.68 mmol), potassium hydroxide (55 mg, 0.98 mmol), and water (0.018 mL, 0.98 mmol). The reaction mixture was heated at 90° C. for 24 h. Additional Pd(P(t-Bu3)2 (5 mg) and cetyltrimethyl-ammonium bromide (3 mg) was added and heating was continued for 18 h. Additional Pd(P(t-Bu3)2 (5 mg) was added, and the reaction was heated to 100° C. for 12 h. The reaction mixture was filtered through a column of silica gel in ethyl acetate and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel (30-40% v/v ethyl acetate/hexane) to give compound 8a (120 mg, 40%) as a colorless solid. ESI-MS m/e 459.2 (M+1).

Provenance & Evidence