To 5-bromo-1H-pyrrolo[2,3-b]pyridine (152, 0.622 g, 3.16 mmol) in 50.0 mL of methanol under nitrogen, (5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (153, 1.05 g, 3.06 mmol) and potassium hydroxide (1.50 g, 26.7 mmol) were added and the reaction stirred at room temperature overnight. The reaction was poured into water, extracted with ethyl acetate, the organic layer dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with a gradient of 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (154, 0.35 g). {5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester was also formed in this procedure and could be isolated and reacted similarly to the following step to form the desired product.
