Sodium Carbonate → HCID 21473696, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (2 g, 5.25 mmol) and 4-chlorophenyl boronic acid (1.17 g, 7.5 mmol)in toluene (20 ml) was added a 2M sodium carbonate solution (7.5 ml). The reaction mixture was stirred under a nitrogen atmosphere, then tetrakis(triphenylphosphine)palladium(0) (0.29 g, 0.25 mmol) was added and the reaction mixture was heated at 90° C. for 18 h. After allowing to cool the reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts were combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. Purification by flash chromatography using hexane/ethyl acetate as eluant gave the title compound as an oil (0.7 g, 39%); δH (CDCl3) 1.5 (9H, s, C(CH3)3), 2.89 (2H, t, J 8.3 Hz, CH2), 3.68 (2H, t, J 8.3 Hz, CH2), 4.61 (2H, s, CH2), and 7.15-7.5 (7H, m, ArH).

Provenance & Evidence