Toluene → (4-Methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine

Participants

Reaction Conditions

Reaction Steps

A sealed tube with a teflon screw cap was charged with 2-bromo-6-oxazol-5-ylpyridine (4.00 g, 17.8 mmol), 2-amino-4-methylpyridine (2.30 g, 21.3 mmol), Pd2(dba)3 (320 mg, 0.349 mmol), (±)-BINAP (440 mg, 0.707 mmol), NaOtBu (2.40 g, 25.0 mmol) and anhydrous toluene (80 ml) and heated to 90° C. with stirring for 1 h. The cooled reaction 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 yellow-orange solid (1.89 g, 42%). 1H NMR (300 MHz, DMSO-d6): δ=9.78 (s, 1H), 8.53 (s, 1H), 8.11 (d, J=5.0 Hz, 1H), 7.84-7.59 (m, 4H), 7.25 (d, J=7.3 Hz, 1H), 6.76 (d, J=5.0 Hz, 1H), 2.32 (s, 3H). (ESI+) m/z 253 (M+H).

Provenance & Evidence