Lithium diisopropylamide → HCID 57795054, compound

Participants

Reaction Steps

To the solution of 3-(pyridin-3-ylmethyl)pyridine (0.085 g, 0.5 mmol) in THF (5 mL) at −78° C. was added LDA (0.3 mL, 1.8 M) and stirred for 1 h. 2-Bromo-6-[(6-bromopyridin-2-yl)(chloro)methyl]pyridine (0.181 g, 0.5 mmol) in THF (2 mL) was added. The mixture was stirred at 0° C. for 1 h. The reaction was quenched with ice and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (50% EtOAc in hexane) to give 2-bromo-6-[1-(6-bromopyridin-2-yl)-2-pyridin-2-yl-2-pyridin-3-ylethyl]pyridine. 1H-NMR (500 MHz, CDCl3) δ 8.58 (d, 1H, J=1.9), 8.47 (d, 1H, J=4.9), 8.30 (dd, 1H, J=4.7, 1.5), 7.95 (d, 1H, J=8.1), 7.44 (td, 1H, J=7.6, 1.7), 7.39 (t, 2H, J=7.7), 7.28-7.33 (m, 2H), 7.20 (d, 1H, J=7.6), 7.15 (dd, 2H, J=7.7, 4.7), 7.10 (dd, 1H, J=7.9, 4.8), 6.97 (dd, 1H, J=7.4, 4.8), 5.45 (d, 1H, J=12.0), 5.29 (d, 1H, J=12.0). LRMS m/z (M+H) Calcd: 497.2, found: 496.9.

Provenance & Evidence