Hydrochloric Acid → HCID 22093480, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-bromo-2-fluoro-benzyl)-4-fluoro-2-hydroxy-5-morpholin-4-yl-benzamide (0.8 g, 2.13 mmol) in acetone (11 mL), was treated with aq 2 N K2CO3 (1.6 mL, 3.20 mmol) and ethyl bromoacetate (0.35 mL, 3.20 mmol), and heated to 50° C. After stirring for 30 min, the reaction was cooled to room temperature and acidified to pH 7 with aq 2 N HCl. The resulting solution was extracted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated to give [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-morpholin-4-yl-phenoxy]-acetic acid ethyl ester (0.8 g, 81%): 1H NMR (DMSO-d6 300 MHz) δ 9.05 (t, J=6 Hz, 1 H), 8.18 (d, J=2.1 Hz, 1 H), 8.09 (ddd, J, =8.4 Hz, J2=2.4 Hz, J3=0.9 Hz, 1 H), 7.79 (d, J=7.8 Hz, 1 H), 7.61 (t, J=8.0 Hz, 1 H), 7.54 (d, J=10.2 Hz, 1 H), 7.15 (d, J=14.1 Hz, 1 H), 4.94 (s, 2 H), 4.63 (d, J=6 Hz, 2 H), 4.14 (q, J=7.2 Hz, 2 H), 3.71 (t, J=4.7 Hz, 4 H), 2.92 (t, J=4.7 Hz, 4 H), 1.16 (t, J=7.2 Hz, 3 H).

Provenance & Evidence