Reaction #1256719

Reaction equation

11

4-(4-iodo-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

18

2-(4-vinyl-phenyl)-malononitrile

PPh3

→

title compound

Yield 55.4%

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

Yield 55.4%

Conditions

Workup

1. 1
   Otherevacuated
2. 2
   workup.ADDITIONNext, dry Et3N (5 mL) and dry DMF (10 mL) were added under an N2 flow
3. 3
   OtherThe Schlenk tube was sealed
4. 4
   Otherthe mixture was degassed by 3 freeze-thaw cycles
5. 5
   TemperatureThe reaction mixture was next cooled to room temperature
6. 6
   workup.ADDITIONpoured into water
7. 7
   Extractionextracted with CH2Cl2 (3×50 mL)
8. 8
   DryingThe organic layer was dried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated in vacuo
11. 11
    OtherThe crude product was then purified by flash chromatography on silica gel
12. 12
    Washeluting with 1:1 hexane

Procedure

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 C26H23N3·1/2 H2O: C, 80.80; H, 6.26; N, 10.87. Found; C, 80.22; H, 6.32; N, 10.28.

Source