Sodium borohydride → HCID 68865134, compound

Participants

Reaction Steps

A mixture of Example 103A (150 mg, 0.38 mmol) and NaBH4 (14.3 mg, 0.38 mmol) in isopropanol (3 mL) was heated to reflux overnight and partitioned between diethyl ether and brine. The organic phase was dried (Na2SO4), filtered, concentrated, dissolved in toluene (5 mL), and treated with p-toluenesulfonic acid. The mixture was heated to reflux for 1 hour, cooled to room temperature, and passed through a silica gel plug with dichloromethane to provide the desired product (95 mg, 68% yield). MS (DCI/NH3) m/e 400 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 9.84 (s, 1H), 7.75 (m, 2H), 7.39 (m, 2H), 7.08 (d, 1H), 6.9 (d, 1H), 6.69 (m, 1H), 6.22 (m, 1H), 2.71 (t, 2H), 2.21 (m, 2H).

Provenance & Evidence