Dimethylformamide → HCID 68524610, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-cyano-indole (0.15 mg, 1.05 mmol) in dry DMF (3.5 mL) sodium hydride (55% in oil) (69 mg, 1.58 mmol) was added in one portion at 0° C. The mixture was stirred at 0° C. for 30 min and (bromomethyl)-cyclopropane (0.133 mL, 1.37 mmol) was added. The resulting mixture was allowed to warm to room temperature, and stirred for 30 min. After completion monitored by TLC, reaction mixture was quenched with ice and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (EtOAc:hexane, 1:9) to give the product as a colorless solid (180 mg, 87%). 1H NMR (CDCl3, 400 MHz,): 0.40 (m, 1H), 0.68 (m, 1H), 0.89 (m, 1H), 4.02 (d, J=6.7 Hz, 2H), 6.60 (d, J=3.2 Hz, 7.98 (s, 1H), 7.36 (d, J=3.2 Hz, 2H), 1H), 7.42 (d, J=3.4 Hz, 2H). 13C NMR (CDCl3, 100 MHz,): 4.14, 11.1, 50.9, 102.2, 110.2, 120.9, 124.3, 126.5, 128.2, 129.8, 137.6.

Provenance & Evidence