Ammonium Chloride → HCID 59655000, compound

Participants

Reaction Steps

A solution of cyclohexylmagnesium chloride (250 ul, 0.50 mmol, 2M in THF) was added to a suspension of cupper (I) bromide-dimethylsulfide (51 mg, 0.25 mmol) in 2 ml of THF at −78° C. under N2. The mixture was warmed to rt until a dark color homogenous solution was observed (ca. 15 min), then re-cooled to −78° C. A solution of trifluoro-methanesulfonic acid 1-benzyl-6-chloro-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester (80 mg, 0.16 mmol) in 2 ml of THF was added to the mixture. The resulting mixture was stirred at −78° C. for 2 h and warmed to rt. Treated with 2 ml of sat. NH4Cl followed by 20 ml H2O, the mixture was extracted with EtOAc (2×20 ml). The combined organic layers were washed with H2O (10 ml), brine (10 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (20-30% EtOAc/hexanes) gave 61 mg (88%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) δ8.08 (br s, 1H), 7.40 (dd, 1H, J=9.2, 2.2 Hz), 7.20-7.34 (m, 6H), 6.42 (s, 1H), 5.53 (s, 2H), 2.98 (br s, 1H), 2.41 (s, 3H), 1.67-1.93 (m, 7H), 1.22-1.40 (m, 3H). Mass spectrum (ESI, m/z): Calcd. for C26H25ClN2O2, 433.2 (M+H), found 433.1.

Provenance & Evidence