Potassium Phosphate, Tribasic → HCID 71239958, compound

Participants

Reaction Steps

An oven-dried flask under argon was charged with the 2-bromo-4-oxazol-5-yl-pyridine (Intermediate II-c, 461 mg, 2.07 mmol), 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine V-d (510 mg, 2.07 mmol), K3PO4 (2.82 g, 13.3 mmol), Pd(OAc)2 (51 mg, 0.225 mmol), Davephos (89 mg, 0.225 mmol) in iPrOH (5 mL) and water (3 mL). After 40 min at 100° C., the mixture was cooled to room temperature, diluted with water and extracted with EtOAc then washed with brine. The organics were dried (MgSO4), filtered and evaporated before purification by column chromatography (SiO2, 30% to 100% EtOAc in cyclohexane) to afford the desired product V-e as an off-white solid (240 mg, 43%). 1H NMR (300 MHz, CDCl3) δ 8.78 (d, J=4.8 Hz, 1H), 8.10 (d, J=4.8 Hz, 1H), 8.01 (s, 1H), 7.59 (d, J=4.9 Hz, 2H), 7.51 (d, J=4.9 Hz, 1H), 6.86 (d, J=4.9 Hz, 1H), 3.88 (s, 3H), 2.16 (s, 3H).

Provenance & Evidence