cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene → tert-butyl 4-{[6-[(Z)-2-ethoxyvinyl]-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of tert-butyl 4-{[6-chloro-2-(trifluoromethyl)pyrimidin-4-yl]amino}piperidine-1-carboxylate (1.0 g, 2.6 mmol, from Step 1), tributyl[(Z)-2-ethoxyvinyl]stannane (0.96 mL, 2.9 mmol, Synthonix Corp.) and tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.13 mmol, Strem) in toluene (3.0 mL) was degassed and then heated to 110° C. for 3 hours, then lowered to 90° C. overnight. The mixture was concentrated and flash chromatographed on a 120 g silica gel cartridge, eluting with a gradient from 0-20% EtOAc in hexanes to afford product as a white solid (0.8 g, 73%). 1H NMR (400 MHz, CDCl3) δ 7.08 (s, 1H), 6.58 (d, J=7.1 Hz, 1H), 5.40 (d, J=7.1 Hz, 1H), 4.98 (br s, 1H), 4.18-4.00 (m, 4H), 3.82 (br s, 1H), 2.94 (t, J=11.7 Hz, 2H), 2.12-1.95 (m, 2H), 1.52-1.31 (m, 14H). 19F NMR (376 MHz, CDCl3) δ −71.77 (s). LCMS (M+H): 417.2.

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