Potassium Carbonate → HCID 86664381, compound

Participants

Reaction Conditions

Reaction Steps

2,2,2-Trifluoro-1-(5-iodo-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone (1MK1, 750 mgs, 1.88 mmoles) was dissolved in toluene (25 mls) and 2-chlorophenyl boronic acid (352 mg, 2.25 mmoles), anhydrous potassium carbonate (311 mg, 2.25 mmoles) and finally palladium tetrakis catalyst (111 mg, 0.099 mmoles, 5 mol %) was added. The reaction mixture was flushed with nitrogen and heated to 95° C. overnight. Starting material was still present therefore further 2-chlorophenyl boronic acid (88 mg, 0.56 mmoles), potassium carbonate (78 mg, 0.56 mmoles) and catalyst (28 mg, 0.025 mmoles) were added and the reaction continued for a further 2 hours. The reaction was then cooled and filtered through a pad of Celite. The filtrate was washed with saturated sodium bicarbonate solution (25 mls), water (25 mls) and brine (25 mls). The organic layer was dried over anhydrous magnesium sulphate, filtered and evaporated to give an oily residue. The oil was triturated with ether followed by isopropanol:hexane 1:1. The dark yellow solid (724 mg, 100% yield) was used without further purification. LC-MS (retention, 4.2 mins M+H 386).

Provenance & Evidence