2-bromo-4-(1-pyrrolidinyl)benzonitrile synthesis

Yield:1189353-46-5 96%

Reaction Conditions:

with potassium carbonate in dimethyl sulfoxide at 100; for 17.5 h;Sealed vial;

Steps:

146

K2CO3 (0.691 g, 5.00 mmol) was added to a solution of 2-bromo-4- fluorobenzonitrile (1 g, 5.00 mmol) and pyrrolidine (0.42 mL, 5.08 mmol) in DMSO (10.00 mL) in a vial. The vial was sealed, and the reaction was stirred at 100 ⁰C (bath temp) for 17.5 h. The reaction mixture was diluted with water (50 mL) and EtOAc (25 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 25 mL). The combined organic layers were washed with brine (2 x 20 mL), dried over Na₂SO₄, filtered, concentrated, and dried under high vacuum to afford the title compound (1.21 g, 96%). LC-MS m/z 251 (M)⁺, 1.11 min (ret time).

References:

WO2011/25799,2011,A1 Location in patent:Page/Page column 107