Potassium Carbonate → HCID 57855463, compound

Participants

Reaction Steps

A mixture of 7-bromo-2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinoline (2.90 g, 10.0 mmol), 4-fluorophenylboronic acid (2.10 g, 15.0 mmol), anhydrous potassium carbonate (4.15 g, 30.0 mmol) and triphenylphosphine (525 mg, 2.0 mmol) was prepared in MeOH (20 ml) and 1,4-dioxane (10 ml). Argon was bubbled for 10 min., then Pd(OAc)2 (112 mg, 0.50 mmol) was added. The resulting mixture was refluxed for 5 hours. The reaction mixture was diluted with Et2O (50 ml) and the resulting suspension was filtered trough a pad of Celite. The filtrate was evaporated under reduced pressure. The residue was taken up with Et2O and washed with water (3×) and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure to give a black oil. After purification by flash chromatography on silica (cHex/EtOAc, gradient from 3/1 to 3/2), the title compound was obtained as a beige solid (2.50 g, 82%). HPLC, Rt: 4.4 min (purity: 98.8%). LC/MS, M+(ESI): 306.2.

Provenance & Evidence