Methanol → Methyl 4-((tert-butoxycarbonyl)amino)nicotinate

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Reaction Steps

Formula 504 where R1, R3 and R4 are H; W, Y and Z are —C═; and X is —N═: To a solution of methanol (100 mL) and N-Boc-4-amino-3-pyridine carboxyaldehyde (8.3 g, 37.3 mmol), were added N-iodosuccinimide (21.0 g, 93.4 mmol) and potassium carbonate (12.9 g, 93.4 mmol) at room temperature. The mixture was stirred for 1 hour and then poured into a saturated Na2S2O3 solution (100 mL). After further dilution with water (100 mL) the mixture was extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the pure desired methyl ester product, 4-tert-butoxycarbonylamino-nicotinic acid methyl ester (9.0 g, 96%). MS (Cl) m/e: 253.1.

Provenance & Evidence