3-Amino-5-methylisoxazole → 1-(5-Methylisoxazol-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

Participants

Reaction Conditions

Reaction Steps

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (100 mg, 0.46 mmol), and triphosgene (47 mg, 0.16 mmol) were dissolved in a mixture of dry pyridine:DCM (4:1) and stirred at room temperature (20° C.) under nitrogen atmosphere for 1 h. 5-methylisoxazol-3-amine (49 mg, 0.50 mmol) dissolved in dry DCM was added dropwise, and stirring allowed overnight. Saturated NaHCO3 solution was added to the reaction mixture, and stirring allowed for 15 mins before partitioning between water and DCM. The organic layer was recovered, dried over MgSO4, filtered and solvent removed in vacuo, affording the title compound (155 mg, 0.45 mmol, 99% yield).

Provenance & Evidence