Pyrrolidine → HCID 22093459, compound

Participants

Reaction Steps

A solution of [4-acetylamino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester (0.114 g, 0.24 mmol) in 10% H2O in 1,4-dioxane (8 mL, 0.03 M) was treated with pyrollidine (0.05 mL, 0.60 mmol) and [(C6 H5)3P]4Pd (0.01 g, 3.6 mol %) was stirred for 6 h. The reaction was diluted with ethyl acetate and washed with 2 N HCl (3×) H2O (2×), saturated aq NaCl, dried over MgSO4, filtered, concentrated and recrystallized from heptane and ethyl acetate to give [4-acetylamino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid (0.055 g, 52%) as a white solid: mp 235° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.93 (br s, 1 H), 9.16 (br t, 1 H), 7.98 (br d, J=2.7 Hz, 1 H), 7.73 (br dd, J, =9.0 Hz, J2=2.7 Hz, 1 H), 7.44–7.20 (m, 2 H), 7.20–7.00 (m, 2 H), 4.80 (s, 2 H), 4.54 br d, J=4.5 Hz, 2 H), 1.99 (s, 3 H).

Provenance & Evidence