Sodium Carbonate → HCID 67995873, compound

Participants

Reaction Conditions

Reaction Steps

A 15-mL pressure tube equipped with a magnetic stirrer and screw cap with a septum was charged with 6e (90 rug, 0.30 mmol), 6f (156 mg, 0.39 mmol), sodium carbonate (95 mg, 0.90 mmol), water (0.5 mL), 1,4-dioxane (1.8 mL), and DMF (0.9 mL). After bubbling nitrogen through the resulting suspension for 30 min, tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) was added; the tube was sealed, and the reaction mixture was heated for 16 h in a 120° C. bath. After this time, the mixture was cooled to room temperature and diluted with ethyl acetate (50 mL) and water (5 mL). The organic layer was separated and concentrated under reduced pressure. The residue was purified by column chromatography on silica to afford a 49% yield (79 mg) of 6g as an off-white solid: mp>300° C.; 1H NMR (500 MHz, DMSO-d6) δ 13.40 (s, 1H), 10.45 (s, 1H), 9.93 (s, 1H), 9.25 (s, 1H), 9.04 (s, 1H), 8.95 (s, 1H), 8.74 (d, 2H, J=3.3 Hz), 8.54 (d, 1H, J=4.2 Hz), 8.33 (d, 1H, J=5.7 Hz), 8.10 (d, 2H, J=3.0 Hz), 8.02 (d, 1H, J=5.4 Hz), 7.69 (m, 1H), 7.53 (m, 1H), 1.43 (s, 9H); MS (ESI+) m/z 538.2 (M+H).

Provenance & Evidence