Trifluoroacetic acid → 11-Cyclohexyl-10-oxo-7,8,9,10-tetrahydro-6H-azepino[1,2-a]indole-3-carboxylic acid

Participants

Reaction Steps

A mixture of TFA (1.0 mL) and TFAA (469 mg, 2.232 mmol) was added dropwise to 1-(4-carboxybutyl)-3-cyclohexyl-1H-indole-6-carboxylic acid (365 mg, 1.063 mmol) at 0° C. The reaction mixture was then warmed to rt. and stirred for 4 hr. Water was then added slowly to quench the reaction and a precipitate formed. This was collected by filtration to provide the product as a yellow-greenish solid, (410 mg, >100% yield). MS m/z 326(MH+); 1H NMR (500 MHz, CD3OD) □ ppm 1.39–1.50 (m, 3 H) 1.73–2.14 (m, 11 H) 2.88 (m, 2 H) 3.45 (m, 1 H) 4.46 (m, 2 H) 7.73 (dd, J=8.54, 1.22 Hz, 1 H) 7.98 (d, J=8.55 Hz, 1 H) 8.21 (s, 1 H).

Provenance & Evidence