Sodium Carbonate → HCID 86613122, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of acetylene 20 (53 mg, 0.121 mmol), 4-(N,N-dimethylamino)phenylboronic acid (30 mg, 0.182 mmol), PdCl2(PPh3)2 (9.0 mg, 0.012 mmol), LiCl (15 mg, 0.363 mmol) and 1.0 M aq. Na2CO3 (300 μL, 0.302 mmol) in EtOH (2 mL) and toluene (2 mL) was stirred for 2 h 45 min. at 105° C. The reaction mixture was then poured onto brine (5 mL) and extracted with ethyl acetate (4×10 mL) and the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm) using water-acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give product 21 as a yellow solid (36.85 mg, 64%); 1H NMR (400 MHz, CDCl3) δ 3.01 (s, 6H), 6.82 (d, J=8.82 Hz, 2H), 7.35-7.42 (m, 3H), 7.45-7.65 (m, 7H), 7.95 (s, 1H), 8.08 (d, J=2.14 Hz, 1H), 8.23 (m, 2H), 8.68 (d, J=2.13 Hz, 1H).

Provenance & Evidence