Sodium Bicarbonate → HCID 10300704, compound

Participants

Reaction Steps

A solution of Example 96C (50 mg, 0.13 mmol) in dichloromethane (20 ml) at −20° C. was treated with borontrifluoridediethyletherate (184 mg, 1.3 mmol) dropwise, stirred for 5 minutes, treated with 5-bromo-2-thienylzincbromide (7.8 ml of 0.5M solution in THF, 3.9 mmol) dropwise over 2 minutes, stirred for 15 minutes, treated with saturated NaHCO3 solution (15ml), extracted with dichloromethane. The extract was concentrated and the concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product. MS (ESI(−)Q1MS) m/z 500 and 502 (M−H)−; 1H NMR (400 MHz, CD3OD) δ 8.29 (d, J=9 Hz, 1H), 7.32 (dd, J=9 Hz, 2 Hz, 1H), 7.21(t, J=9 Hz, 1H), 7.16 (d, J=2 Hz, 1H), 6.88 (t, J=74 Hz, 1H), 6.84-6.89 (m, 3H), 6.59 (dd, J=4 Hz, 1Hz, 1H), 6.39 (s, 1H), 3.01 (s, 3H).

Provenance & Evidence