Ethyl chloroformate → HCID 10274903, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 4-[3-(3-bromophenyl)-benzo[c]isoxazol-5-yl]-pyrimidin-2-ylamine (75 mg; 0.205 mmol) in 1 mL of p-dioxane and 0.5 mL of DMSO, was added 40 μL (45.6 mg, 0.42 mmol) of ethyl chloroformate followed by 73 μL (54.3 mg, 0.42 mmol) of diisopropylethylamine. The reaction was stirred at 50° C., in a sealed vessel, for 8 hours. The solvents were removed under vacuo and the crude material was purified via HPLC with acetonitrile/water/TFA as the eluent. The material was isolated as a yellow powder (30 mg, 32% yield). 1H NMR (500 MHz, DMSO-d6) δ 10.5 (br s,1H), 8.9 (s, 1H), 8.75 (d, 1H), 8.35 (m, 3H), 8.3(s, 1H), 8.0 (d, 1H), 7.89 (t, 2H), 7.65 (t, 1H), 4.2 (q, 2H), 1.26 (t, 3H) in ppm. LC-MS (ES+) m/e=439/441 (M+H)

Provenance & Evidence