3-Bromo-2-methyl-1-propene → HCID 59161724, compound

Participants

Reaction Steps

To a solution of [2,6-bis-(4-trifluoromethylphenyl)-pyridin-4-yl]-acetic acid methyl ester (1.18 g, 2.69 mmol) in THF (30 mL) at −78° C. under argon was added potassium bis(trimethylsilyl)amide (0.5 M solution in toluene, 5.38 mL, 2.69 mmol). After stirring for 30 minutes, 3-bromo-2-methylpropene (273 μL, 2.69 mmol) was added and stirred for an additional 30 minutes. The reaction mixture was allowed to warm up slowly and stirred for another 30 minutes at 0° C. The mixture was then concentrated and purified by column chromatography on silica gel (0-8% ethyl acetate in heptane) to give the product as a white solid (940 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 8.24 (d, J=8.29 Hz, 4H), 7.76 (d, J=8.29 Hz, 4H), 7.74 (s, 2H), 4.79 (d, J=19.59 Hz, 2H), 3.97 (dd, J=6.78, 9.04 Hz, 1H), 3.72 (s, 3H), 2.95 (dd, J=8.85, 14.51 Hz, 1H), 2.56 (dd, J=6.59, 14.51 Hz, 1H), 1.78 (s, 3H). MS m/e 494.2 (M+H)

Provenance & Evidence