Sodium Carbonate → HCID 70167226, compound

Participants

Reaction Conditions

Reaction Steps

Benzene boronic acid (301 mg), tetrakis(triphenylphosphine)palladium(0) (65 mg), lithium chloride (238 mg) and aqueous sodium carbonate solution (2 M, 2.25 cm3) were added to a stirred solution of cis-2-(N-benzylmethylamino)methyl-6-trifluoromethanesulfonyl-1-phenyl-1,2,3,4-tetrahydronaphthalene (1.1 g) in 1,2-dimethoxyethane (60 cm3) under an atmosphere of nitrogen. The stirred mixture was heated at 90° C. for 46 h before being allowed to cool to room temperature. Water (100 cm3) and ethyl acetate (100 cm3) were added and the organic layer was washed with water (3×100 cm3), dried (Na2SO4), and the solvent was removed under reduced pressure. The crude product (908 mg) was purified by column chromatography [silica, eluting with toluene-ethyl acetate (19:1)] to afford the title compound as a gum (452 mg); positive ion ESI (M+H)+ 417.9.

Provenance & Evidence