Sodium Carbonate → (2R)-2-methyl-1-{2-[5-(2-methylphenyl)-1-benzofuran-2-yl]ethyl}pyrrolidine

Participants

Reaction Conditions

Reaction Steps

A portion (˜330 μL) of a solution of the product from Example 115A (650 mg, 2.1 mmol) and tetrakis(triphenylphosphine)palladium (125 mg, 0.11 mmol) in benzene (6.2 mL) was added to a mixture of (2-methylphenyl)boronic acid (˜24 mg, ˜0.18 mmol) in ethanol (150 μL). The mixture was treated with 2.0 M aqueous Na2CO3 (200 μL, 0.4 mmol), and the reaction vial was sealed, placed on a heater-stirrer apparatus, and heated at 75° C. for four days. The mixture was cooled to room temperature, diluted with 1:1 MeOH/DMSO (1 mL), filtered, and purified by HPLC [Waters Nova-Pak HR C18 column (25 mm×100 mm, 6 μm particle size) using a gradient of 10% to 100% MeCN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min.] to provide the title compound. MS (APCI) m/z 320 (M+H)+.

Provenance & Evidence