Sodium Azide → HCID 18617612, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.92 g (9.38 mmol) 3-cyano-5-(2-chloroethyl)indole (reference example 4) and 1.53 g (23.5 mmol) sodium azide in 10 mL DMF is heated to 80° C. for three hours, followed by azeotroping with toluene. The resulting residue is chromatographed (2:1 hexane:ethyl acetate) to provide 1.89 g of the product as a brown solid in 95% yield. 1H NMR (CDCl3): δ 3.03 (2H, t, J=7.1 Hz), 3.57 (2H, t, J=7 Hz), 7.20 (1H, dd, J=8, 1 Hz), 7.43 (1H, d, J=8 Hz), 7.62 (1H, s), 7.73 (1H, d, J=3 Hz), 8.81 (1H, br). MS (ion spray) m/z 212 (M+H)+, 169 (M−N3)+.

Provenance & Evidence