Sodium hydride → HCID 59702051, compound

Participants

Reaction Steps

A solution of 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (5) (232 mg, 0.55 mmol) in dry DMF was added to a suspension of NaH (60% in mineral oil, 24 mg, 0.61 mmol) at room temperature. The solution was stirred at room temperature for 15 min. 4-Fluorobenzylbromide (76 μL, 0.61 mmol) was added to the solution through a syringe and further stirred at room temperature for 1 h. The solution was poured into ice water and the solids formed were filtered, washed by cold water, and dried. The crude product was purified by flash chromatography eluting with 0-2% methanol in CH2Cl2 gradient to yield 207 mg (90%) of 4-(4-fluoro-benzyl)-5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester as white solids. 1H NMR (400 MHz, DMSO-d6) δ 1.28 (t, J=7.2 Hz, 3H), 3.34 (m, 4H), 3.80 (m, 4H), 4.27 (q, J=7.2 Hz, 2H), 5.34 (s, 2H), 7.14-7.18 (m, 3H), 7.29-7.35 (m, 3H), 7.48 (dd, J=1.2, 3.6, Hz, 1H), 7.80 (dd, J=1.2, 5.2 Hz, 1H), 8.04 (d, J=5.6 Hz, 1H) ppm; MS m/z=526 amu (M++1). Anal. (C26H24FN3O4S2) C, H, N.

Provenance & Evidence