2-amino-5-bromo-N-methoxybenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-methoxybenzamide (Compound 26D, 1 g, 4.08 mmol) to afford 169 mg of the title compound (14%). 1H NMR (400 MHz, CD3OD) δ=7.85 (d, J=0.5 Hz, 1H), 7.74 (d, J=0.8 Hz, 1H), 7.54 (d, J=2.0 Hz, 1H), 7.41 (dd, J=2.2, 8.5 Hz, 1H), 6.79 (d, J=8.6 Hz, 1H), 4.25 (t, J=7.0 Hz, 2H), 3.81 (s, 3H), 3.54 (t, J=6.2 Hz, 2H), 2.06 (t, J=6.4 Hz, 2H). MS (ESI): m/z=291.13 [MH]. UPLC: tR=0.85 min (UPLC-TOF: polar—3 min).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared analogously to Compound 3D replacing diethylamine with a mixture of methoxylamine hydrochloride (2.07 g, 24.8 mmol) and triethylamine (6.9 mL, 50 mmol) to afford 2.64 g of the title compound (65%). 1H NMR (400 MHz, CD3OD) δ=7.45 (d, J=2.3 Hz, 1H), 7.27 (dd, J=2.3, 8.8 Hz, 1H), 6.69 (d, J=8.8 Hz, 1H), 3.77 (s, 3H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-methoxybenzamide (Compound 26D, 1 g, 4.08 mmol) to afford 169 mg of the title compound (14%). 1H NMR (400 MHz, CD3OD) δ=7.85 (d, J=0.5 Hz, 1H), 7.74 (d, J=0.8 Hz, 1H), 7.54 (d, J=2.0 Hz, 1H), 7.41 (dd, J=2.2, 8.5 Hz, 1H), 6.79 (d, J=8.6 Hz, 1H), 4.25 (t, J=7.0 Hz, 2H), 3.81 (s, 3H), 3.54 (t, J=6.2 Hz, 2H), 2.06 (t, J=6.4 Hz, 2H). MS (ESI): m/z=291.13 [MH]. UPLC: tR=0.85 min (UPLC-TOF: polar—3 min).