8-Iodo-3-(phenylsulfonyl)quinoline → Tert-butyl 3-(3-(phenylsulfonyl)quinolin-8-yl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-iodo-3-(phenylsulfonyl)quinoline (200 mg, 0.51 mmol, prepared according to WO2003080580) in DMA (1 ml) was added PdCl2(dppf) (8.3 mg, 0.10 mmol; dppf=1,1′-bis(diphenylphosphino)ferrocene) and CuI (11.6 mg, 0.06 mmol), followed by dropwise addition of (1-(tert-butoxycarbonyl)azetidin-3-yl)-zinc(II) iodide (317 mg, 0.91 mmol) in DMA (1 ml) over 10 min. The mixture was then heated at 80° C. for 6 h, then stirred at room temperature for 150 h and quenched with a saturated aqueous solution of NaCl. The reaction mixture was extracted with tert.-butyl-methyl-ether (MTBE). The organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography to give the title compound (54 mg, 25%) as a light yellow oil.

Provenance & Evidence