Tetrahydrofuran → HCID 178437418, compound

Participants

Reaction Steps

To 5-bromo-2-ethyl -7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo-[4,5-b]pyridine (75 mg) in THF (2 mL) at -78° C. was sequentially added ZnCl2 (1.58 mL, 1M/ether), iso-propylmagnesium chloride (0.79 mL, 2M/ether), and tetrakis-triphenylphosphinepalladium (15 mg). After complete addition the reaction was warmed to RT and stirred for 16 hours. Extractive workup (EtOAc, from dilute HOAc), and purification (SiO2, 80/20/1 CH2Cl2 /MeOH/NH4OH) gave 43 mg of a solid. 1H NMR (300 MHz, CD3OD) δ 7.60-7.50 (m, 2 H), 7.45 (t, 2H, J=6.9 Hz), 7.12-7.00 (m, 5H), 5.50 (s, 2H), 3.10 (quintet, 1H, J=6.9 Hz) 2.84 (q, 2H, J=7.5 Hz), 2.59 (s, 3H), 1.31 (d, 6H, J=6.9 Hz), 1.24 (t, 3H, J=7.5 Hz)

Provenance & Evidence