Potassium Phosphate, Tribasic → HCID 59596239, compound

Participants

Reaction Steps

To [3-(3-bromo-4-hydroxy-phenyl)-3-(4-methoxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, E) (364 mg, 0.72 mmol) was added potassium phosphate (303 mg, 1.43 mmol), 3-methoxyphenylboronic acid (163 mg, 1.07 mmol), dichlorobis(triphenylphosphine)palladium(II) (50 mg, 0.072 mmol), and 1,2-dimethoxyethane: water:ethanol (7:3:2, 20 mL). The reaction was placed in a hot bath and heated to reflux. After 10 minutes additional 3-methoxyphenylboronic acid (60 mg) and dichlorobis(triphenylphosphine)palladium(II) (25 mg) were added and the reaction refluxed for 30 minutes. Ethyl acetate was added, salts filtered off, and the filtrate removed of solvent under reduced pressure. The mixture was purified three times; first using 20 g silica eluting with 5% acetone/dichloromethane, second using 20 g silica eluting with dichloromethane then 5% acetone/dichloromethane, and third using 40 g silica eluting with a gradient of hexanes to 50% ethyl acetate/hexanes. The product was removed of solvent under reduced pressure to give the title compounds as a white solid which was placed under high vacuum over night (208 mg, 54%). 1H NMR (300 MHz, DMSO-d6-/TFA-d) δ 8.62 (d, J=7.9 Hz, 1 H), 7.88 (t, J=7.6 Hz, 1 H), 7.78-7.69 (m, 2 H), 7.34-7.29 (m, 4 H), 7.10-7.02 (m, 3 H), 6.95-6.86 (m, 4 H), 3.76 (d, J=2.1 Hz, 6 H), 1.62 (s, 9 H); MS (APCI+) m/z 537 [M+1]+; tR=2.50 min.

Provenance & Evidence