toluene (distilled from sodium)
2,4,6-trimethyl aniline
2-bromo-6-methyl pyridine
diethyl ether
brine
[Pd₂(dba)₃]
dppp (1,3-bis(diphenylphosphino)propane)
NaO^tBu
n-hexane
MgSO₄

Toluene (30 ml) was added to a large schlenk vessel charged with 2,4,6-trimethyl aniline (1.0 g, 7.5 mmol), 2-bromo-6-methyl pyridine (1.0 g, 5.9 mmol) and dppp (102 mg, 0.25 mmol). The schlenk was then vacuum degassed and left under argon. [Pd₂(dba)₃] (101 mg, 0.11 mmol) and NaO^tBu (0.85 g, 8.9 mmol) were added to a schlenk under an argon atmosphere and the toluene mixture added via cannula. The resulting deep red/brown mixture was heated overnight at 100°C with stirring. On cooling to room temperature diethyl ether (50 ml) was added. The resultant dark red mixture was washed with brine (2 x 30 ml), dried over MgSO₄ and concentrated in vacuo. The resulting yellow oily product was precipitated by trituration with n-hexane and cooled to -30°C for 2 hours. The yellow crystalline product was isolated by vacuum filtration (0.95g, 72 %)

¹H NMR (293 K, d⁶-benzene) d 7.23 (t, 1H pyridine, J = 8 Hz), 6.94 (s, 2H mesityl Ar), 6.47 (d, 1H pyridine, J = 7 Hz), 6.05 (s, 1H NH), 5.75 (d, 1H pyridine, J = 7 Hz), 2.40 (s, 3H pyridine CH₃), 2.30 (s, 3H, mesityl CH₃), 2.18 (s, 6H, mesityl CH₃). ¹³C{¹H} NMR (293 K d⁶-benzene) d 158.0 (C_g), 157.6 (C_k), 138.5 (C_i), 137.1 (C_f,b), 136.7 (C_a), 134.3 (C_d), 129.6 (C_c,e), 113.3 (C_jH), 102.6 (C_hH), 24.7 (Me_k), 21.3 (Me_d), 18.7 (Me_b,f). IR (nujol, cm^-1): 3189, 2728, 1594, 1582, 1515, 1456, 1377, 1335, 1261, 1234, 1154, 1092, 1033, 990, 860, 820, 788, 722, 621. Anal. Calcd. for C₁₅H₁₈N₂: C, 79.61, H 8.02, N 12.38. Found: C, 79.12, H, 7.93, N, 11.90. MS (EI) m/z 226 (100%, M⁺), 211 (M⁺-CH3).

J. P. Wolfe, H. Tomori, J. P. Sadihghi, J. Yin, and S. L. Buchwald, J. Org. Chem., 2000, 65, 1158.