Methyl iodide → Methyl 4-bromo-6-(methyloxy)-1,5-naphthyridine-3-carboxylate

Participants

Reaction Steps

To a solution of 4-bromo-6-(methoxy)-[1,5]naphthyridine-3-carboxylic acid (for a synthesis see WO2004058144, Example 53(d)) (8.28 g, 29.3 mmol) in DMF (200 ml) was added K2CO3 (5.934 g, 43 mmol) and iodomethane (2.18 ml, 35 mmol) and the reaction was stirred at rt for 72 h. The reaction was partitioned between EtOAc and water. The organic phase was separated and washed twice more with water. The aqueous phases were re-extracted with EtOAc and this EtOAc phase separated and washed with water. The combined organic phases were dried and evaporated to give the desired product as a solid (7 g, 80%).

Provenance & Evidence