A Schelnk vessel was charged with dry THF (30 ml), diisopropylamine (1.18 ml,8.4 mmol) and the solution was cooled to -78˚C, at which point n-butyllithium (2.8ml, 2.5 M, 7.0 mmol) was added and the resulting solution was stirred for 10 min before being warmed to 0˚C for a further 10 min. The reaction mixture was then cooled again to -78˚C and a solution of 5-methyl-2,2'-bipyridine (1.0 g, 5.9mmol) in dry THF was added dropwise. The resulting maroon solution wasstirred for a 1 h at -78˚C. Chlorotrimethylsilane (0.9 ml, 7.1 mmol) was then added rapidly to the solution and after 1 min the reaction was quenched by the rapid addition of absolute ethanol. The resulting pale yellow/green solution was allowed to warm up to room temperature before a saturated solution of NaHCO₃ (150 ml), was added and the reaction mixture extracted into DCM (3 x 75ml). The organic fractions were combined, washed with brine, dried over sodium sulphate, filtered and solvents removed under reduced pressure to yield the titular product as a white solid that was used without purification. Yeild = 1.89 g 84%

1H NMR (400 MHz, 298 K, CDCl3) δH ppm 8.69 (1H, dq, 3JHH = 4.7 Hz, 4JHH =0.9 Py), 8.41 (2H, m, Py), 8.33 (1H, d, 3JHH = 8.3 Hz, Py), 7.78 (1H, td, 3JHH =University of Warwick | Page 1297.8 Hz, 4JHH = 2.0 Hz, Py), 7.46 (1H, dd, 3JHH = 8.0 Hz 4JHH= 2.5, Hz Py), 7.25(1H, ddd, 3JHH = 7.5 Hz 3JHH = 4.7 Hz 4JHH = 1.2, Py), 2.14 (2H, s, CH2), 0.05(9H, s, SiMe3).

13C{1H} NMR (100 MHz, 298K, CDCl3) δC ppm 156.2, 152.1, 148.9, 148.3,136.6, 136.2, 135.8, 122.9, 120.4, 120.3 (py), 23.8 (CH2), 2.2 (SiCH3).