1,2-Dimethoxyethane → HCID 59135100, compound

Participants

Reaction Conditions

Reaction Steps

In a tube were placed 2-bromo-6-iodo-3-methoxypyridine (700 mg, 2.236 mmol), isopropenylboronic acid (212 mg, 2.460 mmol), DME (7.5 mL), EtOH (2.8 mL), and 1M aq. Na2CO3 (5.6 mL). The mixture was degassed with N2. Next, Pd(PPh3)4 (206 mg, 0.179 mmol) was added and the mixture was degassed again with N2. The tube was sealed and heated at 80° C. for 16 hours. The reaction was then cooled to room temperature, diluted with EtOAc (100 mL), and washed with saturated NaHCO3 and brine (50 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes) afforded 2-bromo-6-isopropenyl-3-methoxypyridine. Rf=0.38 (25% EtOAc/hexanes). LCMS=230.0 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.36 (d, J=8.5 Hz, 1H), 7.07 (d, J=9.4 Hz, 1H), 5.81 (s, 1H), 5.21 (s, 1H), 3.92 (s, 3H), 2.16 (s, 3H).

Provenance & Evidence