Water → (2-Amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester

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Reaction Steps

Hydroxy acetic acid ethyl ester (294 mg, 2.8 mmol) is dissolved in 5.0 mL of DMF and 60% sodium hydride (113 mg, 2.8 mmol) is added at 0° C. The mixture is stirred for 15 min and 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (392 mg, 1.1 mmol) is added. The mixture is warmed up to room temperature for 2.5 hr. Then water (15 mL) is added along with EtOAc (30 mL). The mixture is stirred for 10 min and the aqueous layer is separated and extracted with EtOAc (2×20 mL). The organic layers are combined and concentrated to give (2-amino-5-bromo-pyridin-3-ylmethoxy)-acetic acid ethyl ester.

Provenance & Evidence