Acetonitrile → 3-(2-(2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

The crude product from Example 112D, the mono-(L)-tartaric acid salt of (2R)-2-methylpyrrolidine (306 mg, 1.3 mmol), and Cs2CO3 (652 mg, 2.0 mmol) were stirred in an approximately 0.2 M MeCN solution of (2R)-2-methylpyrrolidine (1.6 mL, 0.3 mmol). The mixture was heated at 40° C. overnight. More Cs2CO3 (326 mg, 1.0 mmol) and acetonitrile (0.5 mL) were added and the reaction was stirred at 40° C. for four days. The mixture was cooled to room temperature, diluted with CH2Cl2, filtered, and concentrated. The residue was chromatographed twice through a short column of silica with a 0 to 5% gradient of MeOH/CH2Cl2 to provide the title compound as an orange-tan gum (28% yield). 1HNMR (300 MHz, CD3OD) δ 1.18 (d, 3H), 1.39-1.54 (m, 1H), 1.75-1.87 (m, 2H), 1.96-2.09 (m, 1H), 2.27-2.39 (m, 1H), 2.46-2.63 (m, 2H), 2.95-3.15 (m, 2H), 3.20-3.35 (m, 2H), 6.63 (s, 1H), 7.49-7.52 (m, 2H), 7.62 (dd, 1H), 7.67 (ddd, 1H), 7.78 (dd, 1H), 7.90 (ddd, 1H), 7.98 (dd, 1H).

Provenance & Evidence