Triphenylphosphine → 2-(4-{2-[4-(3,5-Dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}-phenyl)-malononitrile

Participants

Reaction Conditions

Reaction Steps

A flame-dried sealable Schlenk tube was charged with 11 (3.37 g, 10.0 mmol), 18 (2.52 g, 15.0 mmol), Pd(OAc)2 (224 mg, 1.00 mmol), and PPh3 (262 mg, 1.00 mmol), evacuated, and then backfilled with N2. Next, dry Et3N (5 mL) and dry DMF (10 mL) were added under an N2 flow. The Schlenk tube was sealed, and the mixture was degassed by 3 freeze-thaw cycles and backfilled with N2. The mixture was then covered with aluminum foil and stirred at 100° C. for 2 days. The reaction mixture was next cooled to room temperature, poured into water, neutralized with dilute HCl to pH=7, and extracted with CH2Cl2 (3×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel, eluting with 1:1 hexane:ethyl acetate to give 2.09 g (55.4%) of the title compound as red solid: mp 58-60° C.; 1H NMR (400 MHz, CDCl3): δ 8.405 (s, 2H), 7.640 (d, 2H, J=8.0 Hz), 7.506 (d, 2H, J=8.0 Hz), 7.337 (s, 2H), 7.160 (s, 2H), 1.936 (s, 6H), 1.929 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 148.657, 148.093, 139.804, 137.383, 135.973, 135.218, 130.978, 127.911, 127.757, 126.774, 126.410, 124.863, 111.915, 28.096, 19.988, 16.749; MS (ESI): m/z 378.5 [M++H, 100]; MS (high resolution, EI): m/z 377.1878 [M+]; calcd, 377.1892; Anal. Calcd. for C26H23N3.1/2H2O: C, 80.80; H, 6.26; N, 10.87. Found; C, 80.22; H, 6.32; N, 10.28.

Provenance & Evidence