Sodium borohydride → HCID 86684042, compound

Participants

Reaction Steps

To a solution of 148e (90 mg, 0.141 mmol) in dichloromethane (5 mL) and methanol (5 mL) was added NaBH4 (10.7 mg, 0.282 mmol). After stirring at room temperature for 1 h, the reaction mixture was quenched with aqueous NH4Cl and concentrated under reduced pressure. The residue was extracted with dichloromethane (3×15 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 148 (40 mg, 44%) as a white solid. MS-ESI: [M+H]+ 640.8. 1H NMR (500 MHz, DMSO-d6) δ 8.57 (d, J=5.0 Hz, 1H), 8.54 (d, J=2.5 Hz, 1H), 8.35-8.28 (m, 1H), 8.06 (s, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.78 (dd, J=1.0, 13.0 Hz, 1H), 7.51 (d, J=5.0 Hz, 1H), 7.40 (d, J=2.5 Hz, 1H), 6.01 (s, 1H), 4.90-4.88 (m, 1H), 4.78-4.76 (m, 1H), 4.64-4.62 (m, 1H), 4.42-4.41 (m, 2H), 4.03-3.92 (m, 4H), 3.59 (s, 3H), 3.00-2.96 (m, 1H), 1.40 (s, 9H), 1.04-1.01 (m, 6H).

Provenance & Evidence