Diethylamine → HCID 18398657, compound

Participants

Reaction Steps

To a degassed solution of diethyl 6-bromo-2-methyl-8-quinolylphosphonate (429 mg, 1.2 mmol, obtained from step 1) and 4-hydroxymethylphenylboronic acid (364 mg, 2.4 mmol) in toluene (6 mL) was added Pd2(dba)3 (54.9 mg, 0.06 mmol). The mixture was degassed and Ph3P (125 mg, 0.48 mmol), Et2NH (105 mg, 1.44 mmol), n-propanaol (0.9 mL) and H2O (0.9 m-L) was added. The mixture was heated to reflux for 6 h. Aqueous NaHCO3 was added and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 369 mg (79%) of the title compound.

Provenance & Evidence