2-(Tributylstannyl)pyridine → (4-Methyl-pyridin-2-yl)-[6-(2-pyridin-2-yl-oxazol-5-yl)-pyridin-2-yl]-amine

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Reaction Steps

A mixture of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (44 mg, 0.153 mmol), 2-tri-n-butylstannyl pyridine (68 mg, 0.184 mmol) and Pd(PPh3)4 (18 mg, 0.016 mmol) in toluene (4 ml) was heated to reflux for 18 h and then concentrated in vacuo. The residue was purified by column chromatography on SiO2 eluting with 5% EtOH in DCM to afford the title compound as a pale orange solid (16 mg, 31%). 1H NMR (300 MHz, DMSO-d6): δ=9.85 (s, 1H), 8.76 (d, J=5.0 Hz, 1H), 8.21 (d, J=7.8 Hz, 1H), 8.12 (d, J=5.0 Hz, 1H), 8.03 (t, J=7.8 Hz, 1H), 7.94 (s, 1H), 7.91 (s, 1H), 7.80 (t, J=7.8 Hz, 1H), 7.67 (d, J=8.5, 1H), 7.58 (m, 1H), 7.39 (d, J=7.2 Hz, 1H), 6.78 (d, J=5.0 Hz, 1H), 2.38 (s, 3H). (ESI+) m/z 330 (M+H)+. Retention time=2.29 mins (method 1).

Provenance & Evidence