Water → 6-[5-(4-Cyano-2-methyl-phenyl)-furan-2-yl]-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

Referring now to Scheme 6, a mixture of 1 (680 mg, 4 mmol), 4-bromo-3-methylbenzonitrile (784 mg, 4 mmol), tetrakis(triphenylphosphine)-palladium(0) (228 mg) and potassium acetate (981.5 mg, 10 mmol) in dry DMF (15 mL) was heated under nitrogen at 120° C. for 16 h. The reaction mixture then poured onto cold-water. The precipitate that formed was collected, dissolved in methylene chloride, and the solution was passed through celite to remove Pd. The solution was evaporated, the solid was filtered and purified to afford 28 (SiO2, hexanes/EtOAc, 1:1), yield 40%, mp 233–234° C. 1H nmr (DMSO-d6); δ 2.61 (s, 3H), 7.25 (d, J=3.6 Hz, 1H), 7.51 (d, J=3.6 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.82 (s, 1H). 8.03–8.07 (m, 2H), 8.36 (dd, J=8.1, 2.1 Hz, 1H), 9.02 (d, J=2.1 Hz, 1H). 13C nmr; δ 153.2, 152.7, 151.9, 150.2, 140.8, 135.6, 134.8, 132.5, 129.8, 127.3, 118.3, 117.0, 114.4, 110.2, 106.8, 21.2.

Provenance & Evidence