Methanol → 2-Butyl-7-methyl-1H-imidazo[4,5-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a cooled (-78° C.) stirred solution of 6-bromo-2-butyl-7-methylimidazo[4,5-b]pyridine (98 mg, 0.366 mmol) in THF (4 mL) was added tert-butyl-lithium (0.86 mL of a 1.7M solution in pentane, 1.46 mmol). After 15 minutes, MeOH (0.5 mL and brine were added the mixture was warmed to room temperature and extracted with EtOAc (4×10 mL). Drying (K2CO3), concentration, and purification (SiO2, 100% EtOAc) gave 60 mg (87%) of the title compound as an oil: 1H NMR (300 MHz, CDCl3) δ8.18 (d, 1H, J=5 Hz), 7.08 (d, 1H, J=5 Hz), 3.05 (t, 2H, J=7.6 Hz), 2.72 (s, 3H), 2.03-1.89 (m, 2H), 1.62-1.43 (m, 2H), 0.96 (t, 3H, J=7.8 Hz).

Provenance & Evidence