2-Methyl-5-vinylpyridine → HCID 53242202, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of bis(tri-t-butylphosphino)palladium (25.4 mg, 0.05 mmol; Aldrich), the product of Example 1B (142 mg, 1.19 mmol), sodium t-butoxide (159 mg, 1.66 mmol; Aldrich) and the product of Example 1A (200 mg, 0.66 mmol) was combined with 1,4-dioxane (6 mL). The reaction mixture was purged with nitrogen and stirred at 105° C. for 4 hours in a sealed tube. The mixture was then heated at 105° C. for another 60 hours. The reaction mixture was cooled to room temperature, filtered through a glass microfiber frit, rinsed with CH3OH (3 mL) and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 50-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.54 (s, 3H), 2.56 (s, 3H), 2.90 (t, J=5.8 Hz, 2H), 2.98 (t, J=5.6 Hz, 2H), 3.69 (br s, 2H), 7.02 (t, J=7.6 Hz, 1H), 7.23 (d, J=16.5 Hz, 1H), 7.29-7.33 (m, 2H), 7.40 (d, J=7.3 Hz, 1H), 7.67 (d, J=16.5 Hz, 1H), 8.02 (dd, J=8.2, 2.1 Hz, 1H), 8.61 (d, J=2.1 Hz, 1H); MS (APCI) m/z 304 (M+H)+.

Provenance & Evidence