Hydrochloric Acid → HCID 53251120, compound

Participants

Reaction Conditions

Reaction Steps

Bis(tri-t-butylphosphino)palladium (58 mg, 0.11 mmol; Aldrich), 4-ethynylpyridine, hydrochloric acid (316 mg, 2.26 mmol; Aldrich), MgSO4 (340 mg, 2.83 mmol), sodium t-butoxide (272 mg, 2.83 mmol; Aldrich), the product of Example 1A (300 mg, 1.131 mmol) and triethylamine (0.40 mL, 2.83 mmol) were suspended in dioxane (10 mL). The mixture was purged with a nitrogen stream for 2 minutes, then stirred under nitrogen at 100° C. for 2 hours in a sealed tube. The mixture was cooled to room temperature, filtered though a glass microfiber frit, rinsed with CH3OH (5 mL) and purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 40-99% 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 (400 MHz, methanol-d4) δ ppm 2.56 (s, 3H), 2.90 (t, J=5.8 Hz, 2H), 2.99 (t, J=5.5 Hz, 2H), 3.69 (s, 2H), 7.00-7.06 (m, 1H), 7.29 (dd, J=7.6, 0.9 Hz, 1H), 7.46 (dd, J=7.9, 0.9 Hz, 1H), 7.61-7.66 (m, 2H), 8.53-8.57 (m, 2H); MS (APCI) m/z 288 (M+H)−.

Provenance & Evidence