Dimethylformamide → HCID 69204373, compound

Participants

Reaction Conditions

Reaction Steps

In a 20-mL capacity microwave vessel was combined (E)-3-(3-ethoxy-4-methoxyphenyl)-acrylonitrile (0.41 g, 2.0 mmol), 5-iodo-2-methoxy-phenylamine (0.75 g, 1.5 equiv, 3.0 mmol), Pd(OAc)2 (45 mg, 10 mol %, 0.2 mmol), nBu4NBr (0.71 g, 1.1 equiv, 2.2 mmol), and KOAc (0.49 g, 2.5 equiv, 5.0 mmol) in DMF (8 mL). The mixture was purged with nitrogen gas for 30 seconds and the vessel was sealed. The reaction mixture was stirred in a microwave at 165° C. for 50 min, after which the starting material was consumed (TLC). The mixture was diluted with EtOAc (100 mL), washed with water (2×75 mL), and then brine (50 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The crude material was purified by column chromatography (SiO2, 7:3 hexanes/EtOAc). Concentration of the desired fractions afforded the title compound (Z)-(3-(4-amino-3-methoxy-phenyl)-3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile in 90% yield, as the major isomer of a 92:8 mixture: 1H NMR δ (400 M Hz, CDCl3) 7.02 (dd, 1H, J=8.4, 2.4 Hz), 6.98 (d, 1H, J=2.4 Hz), 6.90 (d, 1H, J=8.4 Hz), 6.75 (d, 1H, J=8.4 Hz), 6.70 (dd, 1H, J=8.4, 2.4 Hz), 6.65 (d, 1H, J=2.0 Hz), 5.51 (s, 1H), 4.08 (q, 2H, J=6.8 Hz), 3.92 (s, 3H), 3.89 (s, 3H), 1.45 (t, 3H, J=6.8 Hz).

Provenance & Evidence