Methanol → [4-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Participants

Reaction Steps

5-Chloro-1H-pyrrolo[2,3-b]pyridine (4, 783.9 mg, 0.005138 mol, prepared as described in Example 4) and 4-(H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-benzaldehyde (137, 1.79 g, 0.00565 mmol) were combined in methanol (100 mL, 2 mol) and potassium hydroxide (2.88 g, 0.0514 mol) was added. The reaction was stirred at room temperature overnight. The reaction was adsorbed onto silica and purified by silica gel column chromatography, eluting with 1-15% methanol:dichloromethane to provide the desired compound as a yellow oil, which was redissolved in 200 mL of 25% ethyl acetate:hexanes and concentrated to provide a yellow solid (138, 1.2 g, 50%). MS (ESI) [M+H+]+=469.1, 471.1.

Provenance & Evidence