Potassium Phosphate, Tribasic → HCID 24875147, compound

Participants

Reaction Steps

To methanesulfonic acid 4-[3-amino-1-(3-bromo-phenyl)-1H-isoindol-1-yl]-phenyl ester (Scheme #6, U) (100 mg, 0.18 mmol)) was added potassium phosphate (112 mg, 0.53 mmol), 3-pyridyl boronic acid (33 mg, 0.26 mmol), dichlorobis(triphenylphosphine)palladium(II) (12 mg, 0.018 mmol) and 1,2-dimethoxyethane: water:ethanol (7:3:2, 3.0 mL). The reaction was heated in an aluminium block at 100° C. for 15 minutes. The mixture was filtered through a syringe filter and the filtrate was removed of solvent under reduced pressure. The resulting residue was dissolved in acetonitrile/water with trifluoroacetic acid, (75:25:0.1, 4 mL), and purified using RP-HPLC AG2 (tR=10.6 min). The combined purified fractions were lyophilized to give the title compound (52.3 mg, 59%). 1H NMR (500 MHz, DMSO-d6/TFA-d) δ 9.23 (d, J=1.6 Hz, 1 H), 8.96 (d, J=5.6 Hz, 1 H), 8.87 (d, J=8.2 Hz, 1 H), 8.37 (d, J=7.8 Hz, 1 H), 8.17 (dd, J=8.2, 5.7 Hz, 1 H), 8.02 (d, J=7.9 Hz, 1 H), 7.90 (dd, J=18.6, 7.8 Hz, 2 H), 7.82 (s, 1 H), 7.77 (t, J=7.6 Hz, 1 H), 7.67 (t, J=7.8 Hz, 1 H), 7.56 (d, J=8.2 Hz, 1 H), 7.41 (s, 4 H), 3.39 (s, 3 H); MS (ES+) m/z 456 [M+1]+; tR=1.42 min.

Provenance & Evidence