Potassium Carbonate → HCID 69299887, compound

Participants

Reaction Steps

A solution of 4-(4′-bromophenylsulfanyl)-N-tert-butoxycarbonyl-proline methyl ester (416 mg, 1 mmol), (4-Dibenzofuran-4-yl-phenyl)boronic acid (302 mg, 1.05 mmol), Pd(PPh3)4 (52 mg, 5% mol) in toluene (10 mL) and ethanol (2.5 mL) was heated until the solution became clear and subsequently treated with 2 M K2CO3 (1.5 mL). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, diluted with ethyl acetate (100 mL). The organic layer was washed successively with 2% aq HCl and sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (2-10% ethyl acetate in heptane) to give 4-(4′-dibenzofuran-4-yl-bipheny-4-ylsulfanyl)-N-tert-butoxycarbonyl-proline methyl ester (410 mg, 73%). 1H NMR (CDCl3), δ 8.01 (m, 3H), 7.95 (d, J=6 Hz, 1H), 7.73 (d, J=7 Hz, 2H), 7.62 (m, 4H), 7.41 (m 5H), 4.37-4.28 (m, 1H), 4.01 (m, 1H), 3.76 (s, 3H), 3.69 (m, 1H), 3.42 (m, 1H), 2.67 (m, 1H), 2.07 (m, 1H), 1.44 (s, 9H). LCMS 580 (M++1).

Provenance & Evidence