Diisopropylamine → 2-methyl-4-(2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile

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Reaction Conditions

Reaction Steps

The product from Example 106C (670 mg, 2.00 mmol), palladium (II) acetate (22 mg, 0.10 mmol), tri-o-tolylphosphine (61 mg, 0.20 mmol), copper(I) iodide (114 mg, 0.60 mmol), and diisopropylamine (2.8 mL, 20 mmol) were dissolved into a 0.1M MeCN solution of (R)-1-but-3-ynyl-2-methylpyrrolidine (30 mL, 3.0 mmol) and heated at 55° C. overnight. The mixture was cooled to room temperature, concentrated under reduced pressure, and chromatographed through a short column of silica with a 10 to 100% gradient of EtOAc/CH2Cl2 to provide the impure title compound as an orange-brown foam (55% yield), a portion of which was purified by HPLC [Waters Nova-Pak HR C18 column (40 mm×100 mm, 6 μm particle size) using a gradient of 10% to 100% MeCN/0.1% aqueous TFA over 12 min (15 min run time) at a flow rate of 70 mL/min.]. TFA salt: MS (AP) m/z 345 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.49(d, 3H), 1.68-1.82 (m, 1H), 1.99-2.23 (m, 2H), 2.30-2.44 (m, 1H), 2.60 (s, 3H), 3.22-3.90 (m, 7H) 6.82 (s, 1H), 7.55-7.87 (m, 6H).

Provenance & Evidence