Toluene → HCID 86676502, compound

Participants

Reaction Steps

A sealed tube was charged with 2,6-dibromopyridine (474 mg, 2.00 mmol), 2-(4-methoxyphenyl)-5-(tributylstannyl)thiazole (920 mg, 2.00 mmol), Pd(PPh3)4 (231 mg, 0.20 mmol), and anhydrous and degazed toluene (9 ml) and heated to 120° C. with stirring for 24 hours. The cooled reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure before purification by dry flash chromatography over SiO2 eluting with EtOAc/cyclohexane 20/80 to give 5-(6-bromopyridin-2-yl)-2-(4-methoxyphenyl)thiazole (410 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.06 (d, J=7.2 Hz, 1H), 7.96 (d, J=8.3 Hz, 2H), 7.82 (t, J=7.8 Hz, 1H), 7.57 (d, J=7.3 Hz, 1H), 7.07 (d, J=8.5 Hz, 2H), 3.83 (s, 3H).

Provenance & Evidence