Hydrochloric Acid → HCID 178505846, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-ethynyl-1-(4-fluorophenyl)-1H-indole (9.6 g) and neat azidotrimethylsilane (21.7 g) was heated in a sealed tube at 170° C. for 24 h. The reaction mixture was cooled to 0° C. and a mixture of dichloromethan (150 mL) and 2 N aqueous sodium hydroxide was added. After stirring at room temperature for 2 h, the mixture was acidified with concentrated hydrochloric acid. The phases were separated and the aqueous phase was extracted with dichloromethane (2×200 mL). The combined organic phases were washed with brine (200 mL), dried (MgSO4) and the volatile solvents evaporated in vacuo affording pure title compound 19a as an oil (11.8 g): 1H NMR (CDCl3) δ 6.80 (d, 1H), 7.25 (t, 2H), 7.40 (d, 1H), 7.55 (dd, 2H), 7.60 (d, 1H), 7.75 (broad d, 1H), 8.05 (s, 1H), 8.20 (broad s, 1H).

Provenance & Evidence