Trimethyltin chloride → 4-Methyl-9-(trimethylstannyl)acridine

Participants

Reaction Steps

A solution of 9-bromo-4-methylacridine 9 (1 g, 3.7 mmol) in 50 ml anhydrous diethyl ether was cooled to −78° C. under nitrogen. To the solution was added 1.6 M n-BuLi in hexanes (0.74 mmol, 0.46 mL) dropwise over a period of 15 min and a 1.0 M solution of Me3SnCl in hexanes (0.81 mL, 0.81 mmol). The reaction solution mixture was allowed to warm to room temperature, stirred for 18 hours and concentrated in vacuo. Purification of the orange residue by flash chromatography (100:10:1 hexanes:ethyl acetate:triethyl amine) afforded 11 (1.1 g, 84%) as a yellow solid. GC-MS revealed contamination of the product with 5-10% 4-methylacridine that could not be separated by chromatography. The stannane was therefore employed in the Stille coupling with 1,8-dibromonaphthalene without further purification. 1H-NMR δ=0.67 (s, 9H), 2.95 (s, 3H), 7.41 (dd, J=6.9 Hz, J=8.8 Hz, 1H), 7.52 (ddd, J=1.4 Hz, J=6.5 Hz, J=6.5 Hz, 1H), 7.61 (d, J=6.9 Hz, 1H), 7.74 (ddd, J=1.4 Hz, J=7.4 Hz, J=7.4 Hz, 1H), 7.97 (d, J=7.9 Hz, 1H), 8.12 (d, J=9.3 Hz, 1H), 8.28 (d, J=7.9 Hz, 1H). 13C-NMR δ=−4.63, 19.51, 125.33, 125.56, 128.42, 128.94, 129.30, 129.93, 131.38, 133.49, 133.62, 138.58, 147.36, 147.53, 156.78.

Provenance & Evidence