Sodium hydride → HCID 59180379, compound

Participants

Reaction Steps

To a solution of 31 (8.45 g; 32.16 mmol) and methyl 3-aminothiophene-2-carboxylate (5.60 g; 35.38 mmol) in tetrahydrofuran (160 mL) at room temperature was added sodium hydride (1.5 g; 38.59 mmol; 60% mineral oil). The reaction mixture was stirred at room temperature under nitrogen for 16 hours (an additional equivalent of sodium hydride was found to be necessary to drive reaction to an acceptable level of completion) and then quenched with water and aqueous hydrochloric acid (2N) and extracted with ethyl acetate. The combined organic phases were successively washed with water and aqueous saturated sodium chloride, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting crude residue was taken up in ethyl acetate. The resulting precipitate was filtered and triturated from diethyl ether to yield the title compound as a light brown solid (3.58 g).

Provenance & Evidence