4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 22287717, compound

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Reaction Steps

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 4-chloro-3-nitrobenzotrifluoride were used. Triethylamine was used as base, absolute ethanol was used as solvent, and the reaction was heated at reflux for 4.5 hours. Column chromatography afforded the title compound (38%) as a red foam: Rf =0.30 in 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]; 13C NMR (CDCl3) δ147.0, 139.7, 135.1, 131.6, 131.0, 129.2, 128.5, 124.7, 124.2, 120.7, 118.6, 116.8, 116.6, 113.6, 112.6, 67.1, 57.4, 40.8, 31.3, 29.2, 21.9. FAB LRMS 419 [MH+]. Anal. calcd for C21H21N4O2.0.6 CH2Cl2 : C, 55.27; H, 4.77; N, 11.94. Found: C, 55.44; H 4.58; N 11.52.

Provenance & Evidence