tert-Butyl piperazine-1-carboxylate → 1,1-Dimethylethyl 4-(5-chloro-8-quinolinyl)-1-piperazinecarboxylate

Temperature

75 °C

A mixture of 5-chloroquinolin-8-yl trifluoromethanesulfonate (1.8 g, 5.78 mmol), Cesium carbonate (2.63 g, 8.09 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.180 g, 0.29 mmol), tert- Butyl 1-piperazinecarboxylate (1.291 g, 6.93 mmol) and Palladium(II) acetate (0.065 g, 0.29 mmol) in THF (30 mL) under a nitrogen atmosphere was stirred at 75 °C for 6h. The solution was cooled to rt and diluted with ether. The mixtture was filtered through celite and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 25-50% EtOAc in heptane, to afford tert-butyl 4-(5-chloroquinolin-8-yl)piperazine-1-carboxylate (0.489 g, 24.34 %) as an oil. 1H NMR (400 MHz, CHLOROFORM- _d_ ) d ppm 1.51 (s, 9 H), 3.28 - 3.37 (m, 4 H), 3.72 - 3.82 (m, 4 H), 7.06 (d, _J_ =7.81 Hz, 1 H), 7.48 - 7.57 (m, 2 H), 8.57 (dd, _J_ =8.59, 1.95 Hz, 1 H), 8.94 (dd, _J_ =4.10, 1.76 Hz, 1 H); MS m/z 348.31 [M+H]+ (ESI).

ORD record

ord-8b2355aecdcf48e08035fb224a453205

Source dataset

750 AstraZeneca ELN dataset

Original link

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