Acetic Acid → HCID 89662814, compound

Participants

Reaction Steps

A mixture of Example 100 (100 mg; 0.22 mmol; 1 eq.), paraformaldehyde (60 mg; 0.66 mmol; 3 eq.), sodium triacetoxyborohydride (93 mg; 0.44 mmol; 2 eq.) and AcOH (13 μL; 0.22 mmol; 1 eq.) in DCE (5 mL) was stirred at 65° C. for 16 hours. 1M NaOH was added and the two phases separated. The aqueous layer was extracted with DCM (2×). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (5% to 20% MeOH in DCM) afforded the title compound (82 mg, 80%) as a colourless oil. 1H NMR (DMSO-d6) δ 7.44-7.32 (m, 1H), 7.24 (dd, J=7.4, 1.7 Hz, 1H), 7.16 (d, J=8.2 Hz, 1H), 7.06-6.96 (m, 1H), 4.58-4.42 (m, 2H), 4.42-4.25 (m, 1H), 2.83 (s, 3H), 2.54 (s, 3H), 2.48-2.34 (m, 2H), 2.15 (br s, 2H), 2.04 (s, 3H), 1.94-1.75 (m, 8H), 1.56 (br s, 2H). HPLC (max plot) 98.6%, Rt 3.15 min. UPLC/MS: (MS+) 468.5 ([M+H]+).

Provenance & Evidence