4-(6-FORMYLPYRIDIN-2-YL)BENZONITRILE, 9& synthesis

Yield:834884-79-6 60%

Reaction Conditions:

with sodium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in methanol;water;toluene at 80;

Steps:

6

To A solution of 6- BROMOPYRIDINE-2-CARBALDEHYDE (3. 85 g, 20. 7 MMOL) and Pd (PPH3) 4 (0. 70 g, 0. 6 MMOL) IN 40 ML of TOLUENE under A nitrogen atmosphere was added 20 ML of 2 M aqueous Na2CO2 and 3. 30 G (22. 7 MMOL) OF 4-CYANOBENZENEBORONIC acid in 10 ML of methanol. The mixture was vigorously stirred at 80 °C overnight. The mixture was cooled and extracted with dichloromethane. The organic LAYERAS dried and concentrated to dryness under reduced pressure to give 2. 60 G (60%) of product, MP 158-159°C. 1H-NMR (DMSO-D6) No. 10. 17 (S, 1 H), 8. 24 (D, 2H, J = 8. 0), 8. 00 (M, 3H), 7. 82 (D, 2H, J = 8. 0) ; 3C-NMR (DMSO-D6) 6 188. 9, 151. 3, 148. 7, 137. 8, 133. 9, 128. 4, 123. 2, 120. 3, 116. 5, 114. 2, 108. 9 ; MS (EI) CALCD. mass for C13H?N20 : 208. 2 ; observed mass 208. 1. ANAL. CALCD. for C, 3H8N2O : C, 74. 99 ; H, 3. 87 ; N, 13. 45. Found : C, 75. 12 ; H, 3. 89 ; N, 13. 35.

References:

WO2005/33065,2005,A1 Location in patent:Page/Page column 42