Potassium Carbonate → HCID 44480908, compound

Participants

Reaction Conditions

Reaction Steps

A sealable tube containing the title compound from Example 2 Step C (0.300 g, 1.25 mmol), 3-pyridylboronic acid (0.200 g, 1.62 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.018 g, 0.025 mmol) and potassium carbonate (0.368 g, 3.75 mmol) was flushed with nitrogen before tort-butanol (14.0 mL) and water (1.6 mL) were added. It was flushed again with nitrogen, sealed tightly and heated to 100° C. overnight. The reaction was then cooled to room temperature, poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-12% methanol in ethyl acetate) provided the title compound: LCMS m/z 239.09 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.72 (s, 1H), 8.46 (d, J=4.2 Hz, 1H), 7.86 (ddd, J=1.8, 1.9, 8.0 Hz, 1H), 7.41-7.39 (m, 2H), 7.35 (dd, J=4.8, 7.9 Hz, 1H), 7.04 (d, J=7.9 Hz, 1H), 2.81 (t, J=7.2 Hz, 2H), 2.35-2.31 (m, 2H), 2.26-2.20 (m, 2H).

Provenance & Evidence