Potassium Carbonate → 2-(4-Bromo-2-fluorophenyl)-2-(4-ethyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetamide

Participants

Reaction Steps

To a mixture of 2-bromo-2-(4-bromo-2-fluorophenyl)acetamide (250 mg, 0.8 mmol) and 4-ethyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (189 mg, 0.8 mmol) in N,N-dimethylformamide (2 mL) at 23° C. was added potassium carbonate (333 mg, 2.4 mmol). The reaction mixture was stirred for 3 h and then was poured into brine (100 mL) and extracted with ether (3×100 mL). The combined organic layers were washed with brine (3×50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue by flash chromatography (0-100% ethyl acetate/hexanes) afforded the title product (214 mg, 62%). MS(ES)+ m/e 428 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.07 (t, J=7.07 Hz, 3 H) 1.65-1.77 (m, 2 H) 1.79-1.91 (m, 2 H) 2.10-2.16 (m, 1 H) 2.44 (br. s., 1 H) 2.54 (s, 1 H) 2.66 (br. s., 1 H) 3.17 (s, 2 H) 3.35 (q, J=7.16 Hz, 2 H) 3.93 (d, J=1.52 Hz, 2 H) 4.39 (s, 1 H) 6.00 (br. s., 1 H) 7.19 (br. s., 1 H) 7.27-7.35 (m, 1 H) 7.39 (t, J=2.27 Hz, 1 H) 7.41 (t, J=2.15 Hz, 1 H).

Provenance & Evidence