Hydrochloric Acid → HCID 10236524, compound

Participants

Reaction Steps

Compound 102 (0.2 g, 0.69 mmol) in a solution consisting of Tol/EtOH/2M Na2CO3 aq (5/1/5) was treated with phenylboronic acid (0.12 g, 1.0 mmol) and cat Pd(PPh3)4 and heated to reflux until TLC analysis indicated complete reaction. The reaction was worked up by acidifying with 2 N HCl aq and extracting with EtOAc. The organic layer was washed with saturated NaHCO3 aq, brine, and dried over MgSO4. After filtering and concentrating, the crude material was chromatographed on silica gel (1:9 EtOAc/hexanes to 4:6 EtOAc/hexanes) and then triturated with hexanes to yield 0.10 g of the desired material: Mp.=167–709° C.; 1H NMR (DMSO-d6) δ 9.98 (br s, 1 H), 9.07 (br s, 1 H), 7.68 (d, 1 H, J=8.5 Hz), 7.4–7.38 (m, 3 H), 7.26–7.22 (m, 2 H), 7.18 (d, 1 H, J=8.7 Hz), 6.90 (dd, 1 H, J=8.5 Hz, 2.5 Hz), 6.72 (d, 1 H, J=2.5 Hz), 6.67 (d, 1 H, J=2.3 Hz), 6.62 (dd, 1 H, J=8.7 Hz, 2.4 Hz), 5.81 (s, 1 H).

Provenance & Evidence