Methanol → Ethyl 7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

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Reaction Steps

A solution of ethyl 7-(2-bromo-3-chloro-6-oxo-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (1.0 g, 2.388 mmol) in tetrahydrofuran (10 ml) under a nitrogen atmosphere at 0° C. was treated slowly with 1M borane tetrahydrofuran complex (11.94 ml, 11.94 mmol) and the resultant solution was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature. The mixture was cooled to 0° C. and treated with borane tetrahydrofuran complex borane (2.4 ml, 2.4 mmol). Once the addition was complete the mixture was stirred at 0° C. for 30 minutes and then at RT. The mixture was cooled in ice and carefully treated with MeOH. The mixture was stirred at room temperature for 1 hour and then evaporated under vacuum to give an oil which was purified by chromatography on silica eluting with 0-100% EtOAc/iso-hexane to afford the title compound;

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