Diisopropyl Ether → 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-5-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

Sodium (3.0 equiv., 735 mmol, 16.9 g) was dissolved in dry methanol (240 ml). DMF (160 ml), CuI (0.15 equiv., 37 mmol, 7.0 g) and N-protected 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-iodo-pyridine (I17) (1.0 equiv., 245 mmol, 73.0 g) were added. The reaction mixture was heated to 80° C. for 3 h. After the mixture had been allowed to cool to room temperature, isopropylether and an aqueous NH4Cl solution (5%) were added, the mixture was stirred overnight. The solids were filtered off over Celite and the filtrate was extracted several times with dichloromethane. The combined organic phases were washed with a 10% aqueous NH4OH solution, dried with MgSO4 and concentrated in vacuo. After drying in high vacuum, 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-methoxy-pyridine (I18) (50 g, yield=100%) was pure enough to be used as such in the next step. 1H NMR (δ, CDCl3): 2.08 (6H, s), 3.91 (3H, s), 5.87 (2H, s), 7.15 (1H, d, J=8.7 Hz), 7.32 (1H, dd, J=8.7, 3.0 Hz), 8.27 (1H, d, J=3.0 Hz)

Provenance & Evidence