Potassium Carbonate → HCID 59736765, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 261a (120 mg, 0.26 mmol) and pyridin-3-yl-3-boronic acid (123 mg, 0.34 mmol) in a 2:1 mixture of DME-water (9 mL), was added Pd(PPh3)4 (22 mg, 0.018 mmol), tri-o-toly phosphine (6 mg, 0.018 mmol) and potassium carbonate (109 mg, 0.79 mmol). The solution was degassed with N2 for 5 minutes and then heated at 80° C. for 15 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×40 mL). The organic layer was separated, dried with sodium sulfate and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluent ethyl acetate. A subsequent trituration was performed with DCM for 15 minutes to yield 262 as a white solid (80 mg, 67% yield). 1H NMR: (DMSO) δ 10.09 (s, 1H), 8.99 (dd, J=2.3, 0.8 Hz, 1H), 8.58 (dd, J=4.7, 1.6 Hz, 1H), 8.38 (s, 1H), 8.33 (d, J=1.4 Hz, 1H), 8.17 (ddd, J=9.6, 3.9, 1.8 Hz, 1H), 7.83 (dd, J=8.5, 1.8 Hz, 1H), 7.53-7.50 (m, 2H), 7.46 (d, J=2.2 Hz, 1H), 7.34 (dd, J=5.1, 1.2 Hz, 1H), 7.31 (dd, J=8.2, 2.2 Hz, 1H), 7.25 (dd, J=3.5, 1.2 Hz, 1H), 7.03 (dd, J=5.1, 3.7 Hz, 1H), 6.81 (d, J=8.4 Hz, 1H), 5.74 (s, 2H).

Provenance & Evidence