Potassium Phosphate, Tribasic → HCID 86665695, compound

Participants

Reaction Steps

A mixture of 6-chloro-4-(methylthio)-2,3′-bipyridine-5-carbonitrile (57.7 mg, 0.220 mmol), 2-formyl-4-methoxyphenylboronic acid (83.4 mg, 0.463 mmol), aqueous potassium phosphate (550 μL, 1.100 mmol) and palladium tetrakis(triphenylphosphine) (16.1 mg, 0.014 mmol) in N,N-dimethylformamide (1 mL) was pumped under vacuum and backfilled with nitrogen twice. After 2 h at 90° C., the mixture was cooled to room temperature, diluted with methanol (2 mL) and filtered to give 6-(2-formyl-4-methoxyphenyl)-4-(methylthio)-2,3′-bipyridine-5-carbonitrile as brown solid (56.9 mg, 62% yield). 1H NMR (500 MHz, CDCl3) δ ppm 9.99 (1H, s), 9.20 (1H, δ, J=1.92 Hz), 8.72 (1H, dd, J=4.67, 1.65 Hz), 8.34 (1H, dt, J=7.97, 1.92 Hz), 7.71 (1H, δ, J=8.52 Hz), 7.57 (1H, δ, J=2.75 Hz), 7.56 (1H, s), 7.45-7.49 (1H, m), 7.44 (1H, dd, J=8.11, 4.81 Hz), 3.95 (3H, s), 2.74 (3H, s); MS (ES+) m/z: 362 (M+H); LC retention time: 3.088 min (analytical HPLC Method A).

Provenance & Evidence