Hydrogen Bromide → 660851-46-7

Participants

Reaction Steps

A solution of Example 1E (1.66 g, 4.1 mmol) in DMF (25 mL) at room temperature was treated sequentially with 48% wt HBr (0.1 mL) and KF (0.48 g, 8.2 mmol). The mixture was stirred for 30 minutes, poured into 1N aqueous HCl (100 mL), and extracted with ethyl acetate (3×80 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 0.97 g (82.2%) of the desired product. MS (ESI(−)) m/z 288 (M−H)−; 1H NMR (500 MHz, DMSO-d6) δ 10.69 (br s, 1H), 10.48 (br s, 1H), 9.64 (s, 1H), 9.13 (d, J=1.3 Hz, 1H), 8.86 (d, J=1.3 Hz, 1H), 8.16 (d, J=2.4 Hz, 1H), 6.93 (dd, J=8.5 and 2.4 Hz, 1H), 6.87 (d, J=8.5 Hz, 1H).

Provenance & Evidence