Trifluoroacetic acid → HCID 57537665, compound

Participants

Reaction Steps

5-[4-chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide was taken up in dichloromethane and 500 μL of trifluoroacetic acid added. The mixture was left at ambient temperature for 10 h and then evaporated. The residue was re-dissolved in 3 mL of dichloromethane and 100 μL of 1,2-ethylenediamine. After 6 h at ambient temperature the mixture was evaporated to dryness. The resulting crude was dissolved in dimethylsulfoxide and purified by mass-triggered reverse phase HPLC to afford 18.2 mg (46 μmol, 33%) of 5-[4-chloro-3-(2-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide as an off-white solid. 1H-NMR [500 MHz, d6-DMSO] δ: 12.50 (s, br., 1H), 8.73 (d, 1H), 8.65 (d, 1H), 8.32 (s, 1H), 7.97 (t, 1H), 7.76 (s, 1H), 7.47 (ddd, 1H), 7.41 (, 1H), 7.28-7.21 (m, 2H), 3.01 (s, 3H), 2.97 (s, 3H); MS [MH+] m/z: 395.

Provenance & Evidence