Sodium Carbonate → HCID 57529013, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing (1S)-(5-{2-[2-(4-bromo-phenyl)-5-methyl-oxazole-4-yl]-ethoxy}-indan-1-yl)-acetic acid ethyl ester (0.100 g, 0.21 mmol), 1,1′-phosphino)ferrocene]dichloro palladium(II) (16.9 mg, 0.02 mmol), and 2,4-dimethoxy-pyrimidin-5-boronic acid (0.076 g, 0.41 mmol) in degassed toluene and dioxane (4:1, 2 mL) was added aqueous 2 M sodium carbonate (0.5 mL). The mixture was heated at 85° C. for 16 hours. The reaction mixture was cool to rt and concentrated under vacuum and the residue was dissolved in methanol and acetonitrile and filtered through a C8 reverse phase extraction cartridge. The filtrated concentrated and the residue was purified by preparative HPLC to obtain [(1S)-5-(2-{2-[4-(2,4-dimethoxy-pyrimidin-5-yl)-phenyl]-5-methyl-oxazol-4-yl}-ethoxy)-indan-1-yl]-acetic acid ethyl ester in 45% yield, (50 mg, 0.09 mmol). 1H NMR (CD3Cl) δ 1.3 (t, 3H), 1.8 (m, 1H), 2.4 (m, 5H), 2.9 (m, 3H) 3.1 (t, 2H), 3.5 (m, 1H), 4.1 (s, 6H), 4.2 (m, 4H), 6.7 (m, 2H), 7.1 (d, 1H) 7.8 (d, 2H), 8.4 (s, 1H); MS (ES) 544 (M+1)+.

Provenance & Evidence