Sodium hydride → HCID 123305347, compound

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Reaction Steps

To dry NaH (67.8 mg, 2.83 mmol) under an Argon atmosphere was added a solution of compound 84b (532 mg, 1.88 mmol) in anhydrous DMF (5 mL) slowly over 2 min. The mixture was stirred at rt for 1 h and then cooled to 0° C. 2-(Trimethylsilyl)ethoxymethyl chloride (0.612 mL, 3.391 mmol) was added dropwise over 2 min. After stirring at rt for 1 h, the mixture was quenched carefully with 1 mL of saturated aqueous NH4Cl and poured into brine (75 mL). The mixture was extracted with EtOAc (3×25 mL) and the combined extracts were washed with water (2×25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a faintly yellow crystalline solid. The solid was purified by flash column chromatography on silica gel (0-40% EtOAc-heptane) to give compound 84c as a white solid. Mass spectrum (LCMS, ESI pos.): Calcd. for C14H20BrN3O2Si, 392.1/394.1 (M+Na). found 392.2/394.1.

Provenance & Evidence