Water → HCID 59924705, compound

Participants

Reaction Steps

2-[(S)-1-Phenylethylamino]-4-[5-iodobenzimidazol-1-yl]pyrimidine (EXAMPLE 271) (50 mg), 1-naphthyl boronic acid (22 mg), potassium carbonate (31 mg), and tetrakis(triphenylphosphine)palladium(0) (5 mg) were dissolved in degassed n-propanol (2.6 mL) and water (0.4 mL) and stirred at 80° C. under argon atmosphere. for 15 hours. Upon cooling, the reaction mixture was filtered through Celite® (the ppt was washed with 10 mL of EtOAc) and evaporated. The residue was purified by preparative thin layer chromatography eluted with 5% MeOH/CH2Cl2 giving 43 mg of the title compound. 1H NMR (500 MHz, CDCl3), δ 8.58 (br s, 1H), 8.40 (s, 1H), 7.96-7.90 (m, 4H), 7.59-7.27 (m, 10H), 6.85 (d, 1H, J=5.5 Hz), 6.45 (br s, 1H), 5.25 (s, 1H), 1.67 (d, 3H, J=7.0 Hz); Mass spectrum (ESI) 442.2 (M+1).

Provenance & Evidence