4-Fluorophenylboronic acid → HCID 59784107, compound

Participants

Reaction Steps

Intermediate 7 (486 mg, 0.89 mmol), 4-fluorophenylboronic acid (625 mg, 4.47 mmol), Cu(OAc)2 (406 mg, 2.24 mmol) and TEA (451 mg, 4.47 mmol) are all weighed into a flask, then dissolved in dry CH2Cl2 (20 mL). This mixture is stirred for 24 h. at room temperature, at which point some of the desired product had formed by LCMS. A further portion of boronic acid (625 mg, 4.47 mmol) is added and the mixture allowed to stir for a further 24 h, making the desired product the major peak, along with unreacted starting material. This reaction mixture is concentrated under reduced pressure, then loaded directly onto a plug of silica which is eluted with 10% Et2O/CH2Cl2 to isolate the desired product. Unreacted starting material remains at the column baseline under these conditions. The title compound is isolated as a off-white foam (188 mg, 33% yield): 1H NMR δ (CDCl3) 6.92-7.42 (m, 8H), 6.74 (v br s, 1H), 6.09 (br d, J=8.4 Hz, 1H), 3.97-5.27 (br m, 6H), 3.35-3.56 (br m, 2H), 2.62-3.16 (br m, 7H), 1.65-2.14 (m, 5H), 1.47 (s, 9H), 1.31 (br d, J=7.1 Hz, 2H), 1.14 (br d, J=7.1 Hz, 1H), 0.98 (brt, J=7.3 Hz, 2H), 0.79 (br d, J=6.7 Hz, 2H), 0.61 (br d, J=6.7 Hz, 2H); LCMS (APCl+) 639.4 (MH+, 100%).

Provenance & Evidence