2-(Tributylstannyl)pyridine → HCID 66977115, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-(5-(4-amino-3-bromo-5-nitrophenyl)pyrimidin-2-yl)-4-ethylpiperidine-4-carboxylate (1.5 g, 3.14 mmol) in DMF (10.0 mL) was added 2-(tributylstannyl)pyridine (1.73 g, 4.72 mmol) and the mixture degassed by purging N2 for 15 min followed by addition of tetrakis(triphenylphosphine)palladium(0) (0.36 g, 0.314 mmol). The reaction mixture was again degassed for 10 min then heated up to 120° C. for 5 h. After completion of reaction, 100 mL ice-cold water was added, extracted with EtOAc (4×100 mL) and the combined organic layer washed with ice-cold water, brine solution respectively, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over neutral alumina using 15% EtOAc:Hexane to obtain the desired product (0.712 g, 47%). 1H NMR (CDCl3): δ 8.68-8.69 (m, 1H), 8.63 (s, 2H), 8.38 (s, 1H), 7.89 (s, 1H), 7.84 (s, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.34-7.36 (m, 1H), 4.65-4.67 (m, 2H), 4.20-4.22 (m, 2H), 3.21-3.25 (m, 2H), 2.30-2.34 (m, 2H), 1.58-1.60 (m, 2H), 1.44-1.46 (m, 2H), 1.30 (t, J=7.20 Hz, 3H) and 0.86 (t, J=7.60 Hz, 3H). MS: 477.44 [M+H]+.

Provenance & Evidence