2-Bromo-4-methylaniline → 1-(2-Bromo-4-methyl-phenyl)-3-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-urea

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 285 mg (1.76 mmol) of 1,1′-carbonyldiimidazole and 5 mg (0.041 mmol) of 4-(dimethylamino)pyridine in N,N-dimethylformamide (3.0 mL) was added 0.22 mL (1.76 mmol) of 2-bromo-4-methylaniline. After stirring for 15 min at 25° C., the reaction was heated to 50° C. At 50° C., a solution of 184 mg (0.88 mmol) of (4S,5S)-amine 1 in N,N-dimethylformamide (1 mL) was added dropwise. The reaction was heated to 100° C. for 4 h and then cooled to 25° C. and partially concentrated under reduced pressure. The mixture was taken up in approximately 100 mL of dichloromethane and washed with water. The organic layers were concentrated to a cream-colored solid that was purified by column chromatography (dichloromethane/ethyl acetate/hexane) to yield 73 mg (20%) of the title compound as a white foam.

Provenance & Evidence