2,4-Dibromopyridine → HCID 118092569, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a solution of 2,4-dibromopyridine (0.25 g, 1.06 mmol) in THF (2 ml) for ˜10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.122 g, 0.106 mmol) was added and the flask sealed with a septa. Bromo (3-ethoxy-3-oxopropyl)zinc (3.17 ml, 1.58 mmol) was added slowly via syringe and the reaction mixture was heated at 85° C. for 16 hours. Upon cooling, the reaction mixture was partitioned between DCM and brine. The organic layer was dried (Na2SO4), concentrated under reduced pressure and the residue was purified by silica gel chromatography (gradient elution with EtOAc/Hexanes 7 to 60%) to give ethyl 3-(4-bromopyridin-2-yl)propanoate as a pale yellow oil. MS ESI calc'd. for C10H13BrNO2 [M+H]+ 258 and 260. found 258 and 260. 1H NMR (500 MHz, CDCl3) δ 8.33 (d, J=5.1 Hz, 1H), 7.39 (bs, 1H), 7.30 (dd, J=5.2, 1.7 Hz, 1H), 4.12 (q, J=6.7 Hz, 2H), 3.08 (t, J=6.5 Hz, 2H), 2.79 (t, J=6.4 Hz, 2H), 1.23 (t, J=6.8 Hz, 3H).

Provenance & Evidence