Triphenylphosphine → 8-{4-Fluoro-3-[2-(4-methanesulfonyl-phenyl)-vinyl]-phenyl}-6-isopropyl-quinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methanesulfonylbenzyl chloride (10 g, 49 mmol) and triphenylphosphine (12.8 g, 49 mmol) in acetonitrile (100 mL) was stirred for 18 h at reflux. The resulting reaction mixture was cooled to 21° C. and the phosphorus salt crystallised from CH3CN/ether. To a suspension of the salt (875 mg, 1.87 mmol) in THF (15 mL) at 0° C. was added potassium tert-butoxide (1M, THF, 1.87 mL, 1.87 mmol) dropwise and the resulting mixture stirred 30 min at 0° C. The mixture was cooled to −78° C. and the 2-fluoro-5-(6-isopropyl-quinolin-8-yl)-benzaldehyde from Step 3 (0.5 g, 1.7 mmol, in THF) was added. After 90 min. at 21° C., the reaction mixture was diluted with HCl 10% and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 60:40) provided the 8-{4-fluoro-3-[2-(4-methanesulfonyl-phenyl)-vinyl]-phenyl}-6-isopropyl-quinoline compound as a mixture of isomer (3:1).

Provenance & Evidence