Sodium Hydroxide → HCID 811100, compound

Participants

Reaction Steps

Compound 1 (710 mg, 1.92 mmol, 1.00 eq) was dissolved in 1N HCl in MeOH (22 mL) and zinc (377 mg, 5.77 mmol, 3.00 eq) was added. The reaction was stirred for 1 hour and additional zinc (251 mg, 3.84 mmol, 2.00 eq) was added to drive the reaction to completion as determined by TLC. The reaction was neutralized with 1N NaOH, filtered and extracted with CH2Cl2 (3×). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 555 mg (85%) of the title compound as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.37 (dd, J=2.7, 0.8 Hz, 1H), 8.34 (dd, J=4.3, 1.7 Hz, 1H), 7.93 (t, J=1.8 Hz, 1H), 7.84 (dt, J=7.9, 1.2 Hz, 1H), 7.63 (ddd, J=8.1, 2.1, 1.0 1H), 7.52 (t, J=7.8 Hz, 1H), 7.43 (m, 2H), 6.94 (t, J=1.8 Hz, 1H), 6.62 (t, J=2.0 Hz, 1H), 6.00 (t, J=2.1 Hz, 1H), 5.37 (s, 2H); ES-MS [M+1]+: 340.1.

Provenance & Evidence