Aniline → HCID 57824997, compound

Participants

Reaction Conditions

Reaction Steps

A dried pressure tube was charged consecutively with (RS)-4-(3-bromo-5-fluoro-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (Building Block AH, 100 mg, 0.3 mmol), toluene (1.5 mL), sodium tert-butylate (52 mg, 0.5 mmol), and tert-butyl x-phos [di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine] (12 mg, 0.03 mmol). The mixture was purged with argon before [tris(dibenzylidenacetone)dipalladium chloroform complex] (8 mg, 0.008 mmol) and aniline (49 mg, 0.5 mmol) were added. The sealed tube was heated at 105° C. for 15 hours. For the working-up, the reaction mixture was cooled and evaporated under reduced pressure. The residue was directly chromatographed on an Isolute Flash NH2 column using a gradient of heptane/ethyl acetate=100/0 to 100/0 as the eluent. There were obtained 49 mg (47% of theory) of (RS)-4-(3-fluoro-5-phenylamino-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine as a white foam; Mass (calculated) C23H22FN3O2 [391]; (found) [M+H]+=392.

Provenance & Evidence