Potassium Phosphate, Tribasic → HCID 135964263, compound

Participants

Reaction Steps

To a flask was added 157 mg (0.250 mmol) of 10-bromo-5,15-bis(2,4,6-trimethylphenyl)porphyrin, (6), 1.06 g (5.00 mmol) of potassium phosphate tribasic, 314 mg (1.76 mmol) of 4-acetamidophenylboronic acid (supplied by Acros), and 70 mL of THF. The suspension was flushed with argon for 10 min, and then 39 mg (0.025 mmol) of tetrakis(triphenylphosphine)palladium(0) was added and the argon flushing procedure continued for an additional 10 min. The reaction mixture was then warmed to reflux under an argon atmosphere for 48 h. The solvent was evaporated at reduced pressure, the residue was redissolved in dichloromethane and washed with water, the organic phase was dried over sodium sulfate, and the solvent was once again evaporated at reduced pressure. The crude product was chromatographed on silica gel (dichloromethane/1% acetone) to give 124 mg (73% yield) of the desired porphyrin. 1H NMR (300 MHz) δ−2.89 (2H, s, N—H), 1.84 (12H, s, Ar—CH3), 2.33 (3H, s, acetyl-CH3), 2.67 (6H, s, Ar—CH3), 7.29 (4H, s, Ar—H), 7.47 (1H, s, N—H), 7.85 (2H, d, J=8 Hz, Ar—H), 8.15 (2H, d, J=8 Hz, Ar—H), 8.72 (2H, d, J=5 Hz, β-H), 8.82 (4H, d, J=5 Hz, β-H), 9.26 (2H, d, J=5 Hz, β-H), 10.11 (1H, s, meso-H); MALDI-TOF-MS m/z calcd for C46H41N5O1 679.33, obsd 679.33.

Provenance & Evidence