Potassium Carbonate → HCID 69326674, compound

Participants

Reaction Steps

A solution of 4-(4′-bromobiphen-4-yloxy)-N-tert-butoxycarbonyl-proline methyl ester (476 mg, 1 mmol), 4-dibenzofuranylboronic acid (222 mg, 1.05 mmol) and 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, filtered and concentrated. Purification by flash column chromatography (2-10% ethyl acetate in heptane) gave 4-(4′-dibenzofuran-4-yl-bipheny-4-yloxy)-N-tert-butoxycarbonyl-proline methyl ester (423 mg, 75%) as a foam. 1H NMR (CDCl3), δ 7.97 (m, 4H), 7.71 (dd, J=1, 8 Hz, 2H), 7.62 (m, 4H), 7.45 (m, 3H), 6.90 (dd, J=1, 9 Hz, 2H), 4.96 (m, 1H), 4.52 (m, 1H), 3.78 (m, 5H), 2.52 (m, 2H), 1.46 (s, 9H). LCMS 464 (M+−100).

Provenance & Evidence