Pyridine → HCID 22093472, compound

Participants

Reaction Steps

A solution of [4-amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester (0.13 g, 0.30 mmol) was dissolved in tetrahydrofuran (2 mL, 0.2 M) along with pyridine (0.05 mL, 0.05 g, 0.61 mmol). This mixture was cooled to 0° C. before treatment with acetic anhydride (0.10 mL, 0.098 g, 0.95 mmol). After stirring at room temperature for 24 h, the reaction mixture was diluted ethyl acetate and sucessively washed with 2 N HCl, saturated aq NaHCO3 and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered and concentrated to give [4-acetylamino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester (0.125 g, 87%): 1H NMR (DMSO-d6, 300 MHz) δ 89.95 (br s, 1 H), 8.94 (br t, J=5.7 Hz, 1 H), 7.98 (d, J=2.7 Hz, 1 H), 7.74 (dd, J1=9.0 Hz, J2=3.0 Hz, 1 H), 7.42–7.24 (m, 2 H), 7.22–7.02 (m, 2 H), 5.88 (m, 1 H), 5.30 (dd, J1=17.1 Hz, J2=1.8 Hz, 1 H), 5.21 (dd, J1=9.0 Hz, J2=1.8 hz, 1 H), 4.97 (s, 2 H), 4.64 (br d, J=5.4 Hz, 2 H), 4.55 (br d, J=6.0 Hz, 2 H), 2.00 (s, 3H).

Provenance & Evidence