1: With sodium t-butanolate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) in toluene 2 h; Heating / reflux; 2: With water in toluene

1: aminoantipyrene With sodium t-butanolate in toluene Dean-StarkInert atmosphere; 2: iodobenzene With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine in toluene T=60°C; 12 h; Inert atmosphere;

copper; aniline T=170°C;

1: 82 percent / Pd(dba)2; (t-Bu)3P / toluene / 8 h / 80 °C 2: 95 percent / aq. acetic acid / 3 h / 50 °C 3: 96 percent / NaBH4 / tetrahydrofuran; methanol View Scheme