Toluene → HCID 53311314, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with 2,6-dibromopyridine (525 mg, 2.21 mmol), 2-[1,3]dioxolan-2-yl-5-tributylstannanyl-thiazole (J. Med. Chem. 2007, 50, 6303) (990 mg, 2.21 mmol), Pd(PPh3)4 (256 mg, 0.22 mmol), [1,1-Bis(diphenylphosphino)ferrocene]palladium(II) chloride. CH2Cl2 (30 mg, 0.036 mmol) and anhydrous and degassed toluene (8 ml) and heated to 110° C. with stirring for 48 h. The cooled reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®, eluting with cyclohexane/ethyl acetate 100/0 to 44/56 to afford the title compound as a white solid (370 mg, 54%). 1H NMR (DMSO-d6, 300 MHz): δ=8.55 (s, 1H), 8.06 (dd, J=7.7-0.7 Hz, 1H), 7.85 (dd, J=7.9-7.7 Hz, 1H), 7.61 (dd, J=7.9-0.7 Hz, 1H), 6.08 (s, 1H), 4.15-4.00 (m, 4H).

Provenance & Evidence