Chlorotrimethylsilane → HCID 58349465, compound

Participants

Reaction Steps

Diisopropylamine (0.770 mL, 5.41 mmol) was added dropwise to nBuLi (2.3 M in hexanes, 2.14 mL, 4.92 mmol) in THF (25 mL) at −78° C. After stirring for 15 minutes, a solution of 4-bromo-6,7-difluoroquinoline (1.20 g, 4.92 mmol) in THF (25 mL) was added slowly via cannula. After stirring an additional 1.5 hours, chlorotrimethylsilane (0.690 mL, 5.40 mmol) was added dropwise. After stirring one additional hour, the solution was poured into saturated NH4Cl (aq) (100 mL) then diluted with water (100 mL) and EtOAc (200 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 0-10% EtOAc/hexanes to afford the title compound as a light yellow solid: 1H NMR (500 MHz, CDCl3): δ 8.60 (d, J=4.7 Hz, 1H); 7.93 (dd, J=10.8, 8.6 Hz, 1H); 7.64 (d, J=4.7 Hz, 1H); 0.49 (s, 9H); LC4: 2.86 min. (M+H) 316.

Provenance & Evidence