3-Butyn-2-amine, 2-methyl- → 1,1-Dimethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-prop-2-ynylamine

Participants

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene (J. Organomet. Chem. 2006, 691 (26), 5725) (200 mg; 0.71 mmol) 1,1-dimethyl-prop-2-ynylamine (350 mg; 4.25 mmol) Pd(PPh3)2Cl2 (99 mg; 0.14 mmol) and Cul (27 mg; 0.14 mmol) are dissolved in DMF/NEt3 (3.5 ml/1.5 ml) and microwaved at 100° C. for 20 minutes. The reaction mixture is evaporated and purified via chromatography (SiO2; TBME/MeOH/M/NH3conc 95:5:0.8) to yield the title compound as yellowish crystals. H-NMR (400 Hz; DMSO-d6): 7.64 (d, 2H); 7.38 (d, 2H); 2.08 (bs, 2H); 1.39 (s, 6H); 1.31 (s, 12H). MS (m/z) ES+: 285 (MH+).

Provenance & Evidence