Water → [6-(2-Benzoxazole-2-yl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine

Participants

Reaction Conditions

Reaction Steps

A sealed tube with a teflon screw cap was charged with a mixture of [6-(2-iodo-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (100 mg, 0.264 mmol), benzoxazole (31 mg, 0.264 mmol), Pd(PPh3)4 (15 mg, 0.013 mmol) and LiOtBu (42 mg, 0.529 mmol) in dry dioxane (5 ml) and heated to 100° C. for 24 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 eluting with 30% EtOAc in cyclohexane to afford the title compound as a beige solid (12 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ 9.88 (s, 1H), 8.14-8.11 (m, 2H), 7.99-7.88 (m, 3H), 7.83 (t, J=7.9 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.61-7.51 (m, 2H), 7.46 (d, J=7.3 Hz, 1H), 6.80 (d, J=5.0 Hz, 1H), 2.41 (s, 3H). (ESI+) m/z 370 (M+H)+. Retention time=2.88 mins (method 1).

Provenance & Evidence