Sodium hydride → HCID 58180048, compound

Participants

Reaction Steps

To a solution of 3-bromo-1H-pyrrole (100 mg, 0.68 mmol) in DMF at 0° C. was added NaH (60% oil dispersion, 81 mg, 2.05 mmol). The reaction mixture was stirred for 1 hour, followed by the addition of 1-(2-chloroethyl)pyrrolidine (108 mg, 0.82 mmol). The reaction mixture was for 6 hours at 100° C. After cooling, the reaction mixture was treated with 20 mL of ice cold water, extracted with EtOAc (3×20 mL), washed with brine solution (20 mL), dried (Na2SO4), filtered, and concentrated under vacuum at 48° C. to obtain crude product. Purification by silica gel chromatography yielded 3-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole (50 mg, 31% yield); 1H-NMR (400 MHz, CHCl3): 6.69 (1H, s), 6.59 (1H, s), 6.12 (1H, s), 3.95 (2H, t), 2.80 (2H, t), 2.51 (4H, m), 1.81 (4H, m).

Provenance & Evidence