4-(Methylsulfonyl)aniline → HCID 90204326, compound

Participants

Reaction Steps

To a solution of [3-(4-formyl-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (30 mg, 0.1 mmol) and 4-methanesulfonylaniline (30 mg, 0.17 mmol) in 1,2-dichloroethane (1 mL) was added sodium trisacetoxy borohydride (50 mg, 0.23 mmol). The reaction mixture was stirred for 14 h and then loaded directly on a silica gel column. Elution with 33% hexane in ethyl acetate provided (3-{4-[(4-methanesulfonyl-phenylamino)-methyl]-phenyl}-isoxazol-4-yl)-carbamic acid tert-butyl ester as a waxy solid. This was dissolved in 4M HCl in dioxane and stirred for 1 h. Removal of volatiles under reduced pressure afforded 3-{4-[(4-methanesulfonyl-phenylamino)-methyl]-phenyl}-isoxazol-4-ylamine hydrochloride as a white solid. MH+=344.3

Provenance & Evidence