Sodium hydride → HCID 15614949, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80% by weight dispersion in mineral oil, 0.347 g, 1.1 eq) was added to a stirred solution of 2-bromo-N-(ethoxycarbonyl)-6-methoxy-5-(trifluoromethyl)-1-naphthalenecarboxamide (4.41 g, 10.5 mmol) in anhydrous tetrahydrofuran (150 mL) at room temperture under a dry nitrogen atmosphere. After 1 hour, the t-butyl bromoacetate (2.54 mL, 1.5 eq) was added and the reaction was heated to 55° C. After 11/2 hours of heating, the reaction was cooled to room temperature and the THF was removed. The residue was suspended in ether (250 mL), washed with water (2×100 mL) and saturated aqueous NaCl (1×50 mL), dried with magnesium sulfate, and the ether was removed. The resultant oil was triturated with petroleum ether (1×50 mL) to provide the title compound as a white powder (4.78 g, 85%). A small samle was recrystallized in ether-petroleum ether to provide white crystals for analysis, m.p. 109.5°-112° C.

Provenance & Evidence