Acetic Acid → HCID 69857170, compound

Participants

Reaction Steps

To a mixture of N-[3,5-dichloro-4-(3-formyl-4-hydroxy-phenoxy)-phenyl]-oxamic acid ethyl ester (30 mg, 0.08 mmol) and aminoindan (10 mg, 0.08 mmol) in dichloroethane (1.0 mL) was added sodium triacetoxyborohydride (22.4 mg, 0.11 mmol) and acetic acid (4.5 mg, 0.08 mmol) in single portions. After stirring at RT for 3 h, the solution became clear and yellow. The solution was quenched with saturated aqueous NaHCO3 (5 mL) and extracted with Et2O (3×10 mL). The combined extracts were dried over Na2SO4, filtered and concentrated to give the crude product as a yellow glass. The crude product was purified by preparative TLC (5% Et2O in CH2Cl2) to afford the title compound as an off-white solid. NMR (400 MHz, CDCl3) d 8.94 (s, 1H), 7.74 (s, 2H), 7.36-7.37 (d, 1H), 7.19-7.25 (m, 4H), 6.75-6.77 (d, 1H), 6.61-6.64 (dd, 1H), 6.54-6.55 (d, 1H), 4.40-4.46 (q, 2H), 4,30-4.33 (t, 1H), 4.05-4.08 (d, 1H), 3.95-3.98 (d, 1H), 2.98-3.06 (m, 1H), 2.81-2.88 (m, 1H), 2.42-2.51 (m, 1H), 1.88-1.96 (m, 1H), 1.41-1.45 (t, 3H). MS Calc.: 514.20, Found: 513.1 (M−1).

Provenance & Evidence