Potassium Phosphate, Tribasic → 4-Chloro-6-(4-methoxyphenyl)-2-(4-phenoxyphenyl)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,6-dichloro-2-(4-phenoxyphenyl)nicotinonitrile (56.8 mg, 0.166 mmol), 4-methoxyphenylboronic acid (26.2 mg, 0.172 mmol), potassium phosphate (0.052 mL, 0.629 mmol) and palladium tetrakis(triphenylphosphine) (9.5 mg, 8.22 μmol) in N,N-dimethylformamide (2 mL) was pumped under vacuum and backfilled with nitrogen twice, and heated to 90° C. under nitrogen. After 19 h at 90° C., the mixture was concentrated. The residue was purified by preparative TLC (30% ethyl acetate in hexanes, Whatman PARTISEL® PLK5F, Silica Gel 150 A with Fluorescent Indicator, size: 20×20 cm, layer thickness: 1000 μM) to give 4-chloro-6-(4-methoxyphenyl)-2-(4-phenoxyphenyl)nicotinonitrile as white solid (17.5 mg, 26% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.10 (2H, δ, J=9.04 Hz), 7.99-8.05 (2H, m), 7.76 (1H, s), 7.40 (2H, t, J=7.91 Hz), 7.19 (1H, t, J=7.40 Hz), 7.12 (4H, dd, J=8.16, 4.14 Hz), 7.02 (2H, δ, J=9.03 Hz), 3.89 (3H, s); MS (ES+) m/z: 413 (M+H); LC retention time: 4.488 min (analytical HPLC Method A).

Provenance & Evidence