Tetrafluoroboric acid → HCID 11152242, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 3 (52.0 mg, 0.145 mmol) in 48% HBF4 (0.75 mL) and water (0.1 mL) was treated with solid NaNO2 (11.9 mg, 0.172 mmol) at 0° C. After stirring for 30 minutes, the layers were allowed to separate and the liquid was layer was removed by pipette. The remaining solid was dried under reduced pressure and slurried in toluene (1.5 mL). The suspension was heated at 100° C. for 2.5 hours, allowed to cool to room temperature, and the toluene was removed by pipette. The residue was treated with 1N NaOH (1 mL) and CHCl3 (1 mL) and stirred for 15 minutes. The phases were allowed to separate and the aqueous layer was extracted with CHCl3 (2×1 mL). The organic layers were combined, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.56 (dt, 1H), 8.12 (d, 2H), 7.98 (d, 2H), 7.84 (br s, 1H), 7.59 (d, 2H), 7.53 (ddd, 1H), 7.40 (d, 2H), 7.33 (ddd, 1H), 1.33 (s, 9H); MS (m/z) 349.

Provenance & Evidence